chiral application guide - hplc · column, compares favorably with polysaccharide-derived chiral...

Regis Technologies

ChiralApplicationGuide

ChiralApplicationGuide

6V O L U M E

DURABLE, HIGH EFFICIENCY CHIRAL COLUMNS

Since 1980, Regis Technologies, Inc. has proven to be a leader inchiral separations and services. Our support system to the

analytical and preparative chromatographer is a model othermanufacturers of chiral products try to emulate. Our technicalexpertise, professional staff, and worldwide distribution network ishighly respected and praised in the chiral community.

Regis offers four different types of Chiral StationaryPhases (CSP’s):• Covalently bonded Pirkle-Type Concept • Protein-based • Covalently bonded 18 Crown-ether

The complete line of Pirkle-Type CSP’s aremanufactured on-site at our cGMP facility inMorton Grove, Illinois. Columns range fromanalytical to preparative in size. Since Regispacks their own columns, custom sized columns areeasily attainable.

Regis maintains an extended inventory of Protein-based columnsmanufactured by ChromTech in the United Kingdom and thecovalently bonded 18 Crown-Ether columns manufactured by RStechin South Korea. Information on these product lines is readilyavailable on our website at www.registech.com.

As evidence of our commitment to the scientist in the lab, Regis ispleased to present its Chiral Application Guide VI. This new guidecontains over 500 specific chiral applications using a variety ofchiral column types. We have also included a few new sections inthis guide. We added a Frequently Asked Question section and aQuick Scheme Method Development section.

For applications not listed in this guide, Regis maintains a dedicatedchiral separations lab and chiral separations scientist. This enablesRegis to offer a Free Chiral Screening Service to the scientificcommunity. For specific column types, services or applications notlisted in this guide, please contact Regis directly or visit our websitefor continuously updated information.

Regis Technologies, Inc.

All Regis Chiral

Separations

products must

meet rigorous

manufacturing and

quality control

specifications

before release.

1

2

Advantages of the Pirkle-Type Chiral Stationary Phases 3

Introduction to Regis Chiral Stationary Phases 4Pirkle Chiral Stationary PhasesProtein-based Chiral Stationary Phases RStech Corporation ChiroSil® RCA(+) and SCA(-)

18 Crown-Ether Chiral Stationary Phases

Regis HPLC Chiral Column Product List 7

Aryl Propionic Acid Non Steroidal Anti-Inflammatory Drugs (NSAIDS) 8

Other Carboxylic Acids 11

Basic Nitrogen 15

Basic Amine 15

Esters, Lactones, Ketones, Anhydrides 16

Amides, Imides, Carbamates, etc. 20

Epoxides 24

Alcohols 25

Diols, Hydroxyketones, etc. 32

Sulfoxides 33

Phosphorous Compounds 36

Atropisomers 39

Optical Switches, Liquid Crystal Components 47

Allenes 48

Organometallic Compounds 53

Agricultural Compounds 56

Miscellaneous Pharmaceuticals 61

Barbiturates, Ureas and Diol Epoxides 74

Natural Products 75

β-Blockers 76

Amino Acids 79

Frequently Asked Questions 82

Quick Scheme Method Development 83

References 86

Index 87Applications by CompoundApplications by Column Type

Chiral Screening Data Sheet 91

C O N T E N T S

CHIRAL HPLC APPLICATION GUIDE VI

Regis Technologies, Inc.3

Advantages of the Pirkle-Type Chiral Stationary Phases

Universal Solvent CapabilityThe entire family of Regis’ Pirkle-Type Chiral Stationary Phases (CSP’s) canbe used in BOTH normal and reversed-phase solvents. Due to the fact that allof the Pirkle-Type CSP’s are covalently bonded, the columns can tolerate allcommonly used mobile phase combinations.

Column DurabilityAnother advantage of covalent bonding is column durability. Listed beloware a few distinct benefits associated with the Pirkle-Type CSP’s:• Long lasting columns• Bonded selector will not leach off the silica gel• Can tolerate sample overload• Can utilize strong solvents for cleaning• Columns are fully reversible• Compatible in SFC and SMB applications

Ability to Invert Elution OrderAll of the Pirkle-Type CSP’s are available in both enantiomeric forms. Thisallows the Chromatographer to invert the elution order of the enantiomers bysimply switching columns. This advantage is essential when determiningenantiomeric purity when the trace enantiomer should elute before the major.Elution order is also important in preparative chromatography because whenthe desired enantiomer elutes first, purity and production efficiencyincreases.

Chromatographic EfficiencyUnlike most Chiral columns on the market, Pirkle-Type Chiral HPLC columnsshow excellent chromatographic efficiency. The high density of binding sitesallows larger amounts of sample to be injected without major changes incolumn performance.

Ease of Scale-upPirkle-Type CSP’s were designed to allow the Chromatographer to scale-uptheir separation from analytical to preparative in a linear fashion. Regis usesthe highest grade silica gels available on the market today. The 5-micronCSP’s are bonded on Exsil®. Our 10-micron and 16-micron CSP’s arebonded on Kromasil®. Synthesis of the chiral selectors, bonding of thedifferent CSP’s, and column production is all performed by Regis in onefacility. This allows Regis total control over the product line. This also allowsRegis to perform special requests for the customer, including custom bondingand custom column packing.

REGIS Introduct ion to Regis Chiral Stat ionary Phases

Pirkle Chiral Stationary Phases

The Pirkle-Concept Chiral Stationary Phases generally fall into three classes: π-electronacceptor/π-electron donors, the π-electron acceptors and the π-electron donors. WithPirkle Phases, chiral recognition occurs at binding sites. Major binding sites areclassified as π-basic or π-acidic aromatic rings, acidic sites, basic sites, and stericinteraction sites. Aromatic rings are potential sites for π-π interactions. Acidic sitessupply hydrogens for potential intermolecular hydrogen bonds-the hydrogen is often anamido proton (N-H) from an amide, carbamate, urea, or amine. Basic sites, such as π-electrons, sulfinyl or phosphinyl oxygens, and hydroxy or ether oxygens, may also beinvolved in hydrogen bond formation. Steric interactions may also occur between largegroups.

π-Electron Acceptor/π-Electron Donor Phases

• WHELK-O 1• WHELK-O 2• ULMO

The latest and most revolutionary addition to the Pirkle-Concept series is the π-electronacceptor/π-electron donor phase. This concept is an innovative incorporation of bothπ-acceptor and π-donor characteristics, resulting in a phase that can be used for a widevariety of compound groups.

WHELK-O 1The Whelk-O 1 Chiral Stationary Phase is based on 1-(3,5-Dinitrobenzamido)-1,2,3,4,-tetrahydrophenanthrene. This phase allows separation of underivatizedracemates from a number of families including amides, epoxides, esters, ureas,carbamates, ethers, aziridines, phosphonates, aldehydes, ketones, carboxylic acids,and alcohols.

The Whelk-O 1 was originally designed for the separation of underivatized non-steroidal anti-inflammatory drugs (NSAIDs). This π-electron acceptor/π-electron donorphase exhibits an extraordinary degree of generality, allowing resolution of a widevariety of underivatized racemates. This broad versatility observed on the Whelk-O 1column, compares favorably with polysaccharide-derived chiral stationary phases. Inaddition, because of the Whelk-O 1’s covalent nature, this chiral phase is compatiblewith all commonly used mobile phases, including aqueous systems-a distinct advantageover polysaccharide-derived chiral stationary phases. Other advantages includecolumn durability, excellent efficiency, elution order inversion allowing availability ofboth enantiomeric forms, and excellent preparative capacity.

4 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/

less stableadsorbate

(S,S)(S,S)(S)

(R)

a) Schematic diagram showing keyfunctional groups of the Whelk-O 1 involved in chiral recognition.

b) Schematic diagram showinggeneralized structure of analytes whichare resolved on the Whelk-O 1.

a) b)

more stableadsorbate

DNB

H-bond donor

H-bond acceptorTetrahydro-phenanthreneπ system

Dinitrobenzamideπ-system

Conjugated π-system

Whelk-O 1

WHELK-O 2The Whelk-O 2 is the covalent trifunctional version of the Whelk-O 1. The Whelk-O 2retains the same chiral selector but modifies the support to silica from a monofunctionallinkage to a trifunctional. In most cases, the enantioselectivity remains the sameallowing the separation of the analogous family of racemates as does the Whelk-O 1.

Whelk-O 2 was designed to enhance the stability of the stationary phase due to hydrolysis while using strong organic modifiers such as trifluoroacetic acid. TheWhelk-O 2 is ideal for preparative separations since the material is bonded on 10 µm100 Å spherical Kromasil silica. This allows the preparative chromatographer toperform method development on their analytical column and immediately scale-up tolarger diameter columns.

ULMOThe ULMO chiral stationary phase was developed by Austrian Researchers, Uray,Lindner, and Maier. This CSP has a general ability to separate the enantiomers of manyracemate classes, and is particularly good at separating the enantiomers of arylcarbinols.

The ULMO CSP is based on a 3,5-Dinitrobenzoyl derivative of diphenylethylene-diamine.

π-Electron Acceptor Phases

• DACH-DNB• Pirkle 1-J• α-Burke 2• β-Gem 1• Leucine• Phenylglycine

The π-electron acceptor Pirkle Chiral Stationary Phases can be used to separate a widerange of enantiomers without derivatization, as demonstrated for the following classesof solutes: secondary benzyl alcohols, mandelic acid analogs, α-hydroxy-α-aryl phosphates, α-tetralol analogs, propranolol analogs, β-hydroxy-aryl sulfoxides,alkyl-aryl sulfoxides, diaryl sulfoxides, aryl-substituted cyclic phthalides, aryl-substitutedlactams, aryl-substituted succinimides, aryl-substituted hydantoins, bi-β-naphthol and itsanalogs, and α-aryl acetamides.

DACH-DNBThe innovative DACH-DNB CSP was designed by Italian chemists Dr. FrancescoGasparrini, Misiti and Villani at Rome University “La Sapienza.” The DACH-DNB CSP;which contains the 3,5-dinitrobenzoyl derivative of 1,2-diaminocyclohexane, has beenfound to resolve a broad range of racemate classes including amides, alcohols, esters,ketones, acids, sulfoxides, phosphine oxides, selenoxides, phosponates,thiophosphineoxides, phosphineselenides, phosphine-boranes, β-lactams, organo-metallics, atropisomers and heterocycles.

PIRKLE 1-JThe Pirkle 1-J CSP is based on 3-(3,5-Dinitrobenzamido)-4-pheny-β-lactam. This unusualβ-lactam structure significantly alters its molecular recognition properties. The Pirkle 1Jis useful for the direct separation of underivatized β-blocker enantiomers. It can alsobe used for the separation of the enantiomers of arylpropionic acid NSAID’s as wellas other drugs.

REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/ 5

Whelk-O 2

ULMO

DACH-DNB

Pirkle 1-J

Introduct ion to Regis Chiral Stat ionary Phases REGIS

REGIS Introduct ion to Regis Chiral Stat ionary Phases

α-BURKE 2The α-Burke 2 phase, first prepared by J. A. Burke III, a graduate student of Dr. Pirkle, isderived from dimethyl N-3,5-dinitro-benzoyl-α-amino-2,2-dimethyl-4-pentenylphosphonate. The α-Burke 2 has been specifically designed to directly separate theenantiomers of β-blockers without chemical derivatization, but this chiral phase is notlimited solely to the separation of β-blocker enantiomers. It also resolves the enantiomersof many compounds separated on π-acceptor Pirkle type chiral stationary phases.

β-GEM 1β-Gem 1 is a π-acceptor chiral stationary phase and is derived from N-3,5-dinitrobenzoyl-3-amino-3-phenyl-2-(1,1-dimethylethyl)-propanoate.

For a great many analytes, this chiral phase considerably outperforms its widely usedanalog, phenylglycine. It can separate anilide derivatives of a wide variety of chiralcarboxylic acids, including nonsteroidal anti-inflammatory agents.

LEUCINEThe leucine CSP is based on the 3,5-dinitrobenzoyl derivative of leucine. This π-acceptorphase demonstrates enhanced enantioselectivities for several classes of compounds,including benzodiazapines.

PHENYLGLYCINEPhenylglycine is based on the 3,5-dinitrobenzoyl derivative of phenylglycine.

This CSP resolves a wide variety of compounds which contain π-basic groups. Theseinclude: aryl-substituted cyclic sulfoxides, bi-β-naphthol and its analogs, α-indanol and α-tetralol analogs, and aryl-substituted hydantoins.

Protein-Based Chiral Stationary Phases

Regis Technologies carries a line of protein-based chiral columns manufactured byChromTech AB, United Kingdom. For additional product information and a Protein-BasedChiral Stationary Phase application guide, please contact Regis directly.• Chiral AGP (α-glycoprotein)• Chiral CBH (cellobiohydrolase)• Chiral HSA (human serum albumin)

RStech Corporation ChiroSil® RCA(+) and SCA(-) 18Crown-Ether Chiral Stationary Phases• ChiroSil RCA(+)• ChiroSil SCA (-)

Developed by RStech Corporation in Daejeon, Korea, the ChiroSil phase is the newestaddition to our chiral line of columns. This phase is prepared by a covalent trifunctionalbonding of (+) or (-)-(18-Crown-6)-tetracarboxylic acid as the chiral selector.

This phase which is available in analytical as well as preparative columns, is an excellentchoice for the separation of amino acids and compounds containing primary amines.

Like our other line of columns, this phase is highly durable, has universal solventcompatibility, and has the ability to invert elution order.

As described above, Regis’ Chiral columns can be used to separate a wide variety ofenantiomers in numerous compound groups. Please refer to the Product List on page 7for particular column types, sizes, configurations and product numbers. Consult theapplication separation data section that begins on page 8 for information regardingspecific chiral separations on a wide variety of compounds. See Application Indexes onpage 87.


Phenylglycine

Leucine

ChiroSil

β-Gem 1

α-Burke 2

Regis Chiral Column Product Lis t REGIS


PRODUCT PARTICLE SIZE COLUMN DIMENSIONS PRODUCT#

(R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 4.6 mm 786201(R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 10.0 mm 786202(R,R)-Whelk-O 1 5 µm, 100 Å 25 cm x 30.0 mm 786205(S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 4.6 mm 786101(S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 10.0 mm 786102(S,S)-Whelk-O 1 5 µm, 100 Å 25 cm x 30.0 mm 786105

(R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 4.6 mm 786515(R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 10.0 mm 786525(R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 21.1 mm 786535(R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 21.1 mm 786545(R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 30.0 mm 786708(R,R)-Whelk-O 1 10 µm, 100 Å 25 cm x 50.0 mm 786709(R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 30.0 mm 786713(R,R)-Whelk-O 1 10 µm, 100 Å 50 cm x 50.0 mm 786710(S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 4.6 mm 786615(S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 10.0 mm 786625(S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 21.1mm 786635(S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 21.1 mm 786645(S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 30.0 mm 786702(S,S)-Whelk-O 1 10 µm, 100 Å 25 cm x 50.0 mm 786703(S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 30.0 mm 786716(S,S)-Whelk-O 1 10 µm, 100 Å 50 cm x 50.0 mm 786704

(R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 4.6 mm 786315(R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 10.0 mm 786325(R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 21.1 mm 786335(R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 21.1 mm 786345(R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 30.0 mm 786727(R,R)-Whelk-O 2 10 µm, 100 Å 25 cm x 50.0 mm 786728(R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 30.0 mm 786732(R,R)-Whelk-O 2 10 µm, 100 Å 50 cm x 50.0 mm 786729(S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 4.6 mm 786415(S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 10.0 mm 786425(S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 21.1mm 786435(S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 21.1 mm 786445(S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 30.0 mm 786721(S,S)-Whelk-O 2 10 µm, 100 Å 25 cm x 50.0 mm 786722(S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 30.0 mm 786736(S,S)-Whelk-O 2 10 µm, 100 Å 50 cm x 50.0 mm 786723

(R,R)-ULMO 5 µm, 100 Å 25 cm x 4.6 mm 787200(R,R)-ULMO 5 µm, 100 Å 25 cm x 10.0 mm 787201(R,R)-ULMO 5 µm, 100 Å 25 cm x 30.0 mm 787203(S,S)-ULMO 5 µm, 100 Å 25 cm x 4.6 mm 787100(S,S)-ULMO 5 µm, 100 Å 25 cm x 10.0 mm 787101(S,S)-ULMO 5 µm, 100 Å 25 cm x 30.0 mm 787103

(R,R)-ULMO 10 µm, 100 Å 25 cm x 21.1 mm 787202(R,R)-ULMO 10 µm, 100 Å 25 cm x 30.0 mm 787707(R,R)-ULMO 10 µm, 100 Å 25 cm x 50.0 mm 787708(R,R)-ULMO 10 µm, 100 Å 50 cm x 30.0 mm 787712(R,R)-ULMO 10 µm, 100 Å 50 cm x 50.0 mm 787709(S,S)-ULMO 10 µm, 100 Å 25 cm x 21.1 mm 787102(S,S)-ULMO 10 µm, 100 Å 25 cm x 30.0 mm 787701(S,S)-ULMO 10 µm, 100 Å 25 cm x 50.0 mm 787702(S,S)-ULMO 10 µm, 100 Å 50 cm x 30.0 mm 787715(S,S)-ULMO 10 µm, 100 Å 50 cm x 50.0 mm 787703

PRODUCT PARTICLE SIZE COLUMN DIMENSIONS PRODUCT#

(R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 4.6 mm 788101(R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 10.0 mm 788102(R,R)-DACH-DNB 5 µm, 100 Å 25 cm x 30.0 mm 788104(S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 4.6 mm 788201(S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 10.0 mm 788202(S,S)-DACH-DNB 5 µm, 100 Å 25 cm x 30.0 mm 788204

(R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 21.1 mm 788103(R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 30.0 mm 788707(R,R)-DACH-DNB 10 µm, 100 Å 25 cm x 50.0 mm 788708(R,R)-DACH-DNB 10 µm, 100 Å 50 cm x 30.0 mm 788712(R,R)-DACH-DNB 10 µm, 100 Å 50 cm x 50.0 mm 788709(S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 21.1 mm 788203(S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 30.0 mm 788701(S,S)-DACH-DNB 10 µm, 100 Å 25 cm x 50.0 mm 788702(S,S)-DACH-DNB 10 µm, 100 Å 50 cm x 30.0 mm 788715(S,S)-DACH-DNB 10 µm, 100 Å 50 cm x 50.0 mm 788705

(3R,4S)-Pirkle 1-J 5 µm, 100 Å 25 cm x 4.6 mm 731044(3R,4S)-Pirkle 1-J 5 µm, 100 Å 25 cm x 10.0 mm 731244(3S,4R)-Pirkle 1-J 5 µm, 100 Å 25 cm x 4.6 mm 731045(3S,4R)-Pirkle 1-J 5 µm, 100 Å 25 cm x 10.0 mm 731245

(R,R)-α-Burke 2 5 µm, 100 Å 25 cm x 4.6 mm 735035(R,R)-α-Burke 2 5 µm, 100 Å 25 cm x 10.0 mm 735235(S,S)-α-Burke 2 5 µm, 100 Å 25 cm x 4.6 mm 735037(S,S)-α-Burke 2 5 µm, 100 Å 25 cm x 10.0 mm 735237

(R,R)-β-Gem 1 5 µm, 100 Å 25 cm x 4.6 mm 731043(R,R)-β-Gem 1 5 µm, 100 Å 25 cm x 10.0 mm 731243(S,S)-β-Gem 1 5 µm, 100 Å 25 cm x 4.6 mm 731029(S,S)-β-Gem 1 5 µm, 100 Å 25 cm x 10.0 mm 731229

D-Leucine 5 µm, 100 Å 25 cm x 4.6 mm 731054D-Leucine 5 µm, 100 Å 25 cm x 10.0 mm 731254L-Leucine 5 µm, 100 Å 25 cm x 4.6 mm 731041L-Leucine 5 µm, 100 Å 25 cm x 10.0 mm 731241

D-Phenylglycine 5 µm, 100 Å 25 cm x 4.6 mm 731021D-Phenylglycine 5 µm, 100 Å 25 cm x 10.0 mm 731221L-Phenylglycine 5 µm, 100 Å 25 cm x 4.6 mm 731024L-Phenylglycine 5 µm, 100 Å 25 cm x 10.0 mm 731224

Chiral AGP 5 µm, 300 Å 10 cm x 4.0 mm 732200Chiral AGP 5 µm, 300 Å 15 cm x 4.0 mm 732199Chiral CBH 5 µm, 300 Å 10 cm x 4.0 mm 732350Chiral CBH 5 µm, 300 Å 15 cm x 4.0 mm 732351Chiral HSA 5 µm, 300 Å 10 cm x 4.0 mm 732240Chiral HSA 5 µm, 300 Å 15 cm x 4.0 mm 732239

ChiroSil® RCA(+) 5 µm, 100 Å 15 cm x 4.6 mm 799001ChiroSil® RCA(+) 5 µm, 100 Å 25 cm x 4.6 mm 799002ChiroSil® SCA(-) 5 µm, 100 Å 15 cm x 4.6 mm 799101ChiroSil® SCA(-) 5 µm, 100 Å 25 cm x 4.6 mm 799102

Bulk material is available for all Chiral Stationary Phases

For column dimensions not listed, please contact Regis

NOTE: All columns (except the protein-based columns) listed contain chiral stationary phases that are covalently bound on 5 µm or 10 µm 100 Åspherical silica. A large variety of column dimensions and/or particle sizes are available upon request.

REGIS Aryl Propionic Acid Non-Steroidal Anti-Inflammatory Drugs (NSAIDs)


Ketoprofen Naproxen (semi prep)

Cicloprofen

Etodolac

Tiaprofenic Acid

Fenoprofen

Ketoprofen as 1-naphthylamidePirprofen

KetoprofenColumn = (R,R)-Whelk-O 1

25 cm x 4.6 mmMobile Phase = (47/47/6)

CH2Cl2/Hexane/Ethanol +0.01 M Ammonium Acetate

Flow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 11.0 mink'1 = 3.63α = 1.35reference 46

CH3

OH

OO

H3C

Naproxen (semi prep on analytical column)

80:20:0.5 hexane/IPA/HOAc1 ml/min; 300 nmRun Time = 18 mininject 400 µl @

31.5 mg/ml = 12.6 mg4.6 mm x 25 cm Whelk-O 1reference 6

FenoprofenColumn = (R,R)-Whelk-O 1

25 cm x 4.6 mmMobile Phase = (98/2)

Hexane/IPA +0.1% Acetic Acid


EtodolacColumn = (S,S)-ULMO


Hexane/IPA + 0.1% TFAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 14.5 mink'1 = 2.43α = 1.50reference 48

Cicloprofen20% IPA/hex, 1g/L NH4OAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.16α = 2.15reference 4

CH3

OH

O

Tiaprofenic Acid20% IPA/hex, 1g/L NH4OAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.02α = 1.09reference 4

CH3

OH

O

SO

CH3

OH

ON

Cl

Pirprofen20% IPA/hex, 1g/LNH4OAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.85α = 1.81reference 4

Column: (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (70/30)

Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 230 nmRun Time = 13 mink'1 = 1.51α = 1.25reference 48

Aryl Propionic Acid Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) REGISNaproxen (R:S=30:70) Cicloprofen

Naproxen (Normal Phase)

Naproxen (Reversed Phase)

Flurbiprofen

Ibuprofen

Naproxen Diisopropyl AmideLoxoprofen

Column = (S,S)-ULMO25 cm x 4.6 mmMobile Phase (90/10)

Heptane/IPA + 0.1% TFAFlow Rate = 1.0 mL/minDetection = UV 230 nmRun Time = 8.5 mink'1 = 1.54α = 1.34reference 48

CH3

OH

O

Cicloprofen70:30:0.5 hexane/IPA/HOAc1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.48α = 1.35reference 26

IbuprofenColumn = (R,R)-Whelko-O 1

25 cm x 4.6 mmMobile Phase: (90/10)

Hexane/IPA +0.01 M Ammonium Acetate


FlurbiprofenColumn = (R,R)-Whelko-O 1


Hexane/IPA +0.01 M Ammonium Acetate


Naproxen (Reversed Phase)Column = (R,R)-Whelko-O 1


CH3OH/H2O + 0.1% Acetic Acid


Naproxen (Normal Phase)Column = (R,R)-Whelko-O 1


Hexane/IPA + 0.1% Acetic Acid


Naproxen Diisopropyl Amide10%EtOH/hex1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.23α = 1.53reference 26

LoxoprofenColumn = (R,R)-Whelko-O 1


Hexane/Ethanol +0.01 M Ammonium Acetate



H3CO

CH3

N

O

REGIS Aryl Propionic Acid Non-Steroidal Anti-Inflammatory Drugs (NSAIDs)

3,5-Dimethylanilide-R,S-Ibuprofen Naproxen Methyl Ester

Naproxen

Indoprofen

α-Trityl-2-naphthalene Propionic Acid

Naproxen Methyl Amide

Column = (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase = (85/15)

Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 13.0 mink'1 = 2.91α = 1.36reference 46

H3CO

CH3

OCH3

O

Naproxen Methyl Ester20% IPA/hex, 1g/L NH4OAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.42α = 1.42reference 14

H3CO

CH3

N

O

CH3

H

Naproxen Methyl Amide20% IPA/hex, 1g/L NH4OAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 18.73α = 1.41reference 14

IndoprofenColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (80/20)

Hexane/Ethanol + 0.01 M Ammonium Acetate

Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time 17.0 mink'1 = 8.93α = 1.32reference 46

Rebamipide2-(4-Hydroxy-Phenoxy) Propionic Acid2-(4-Hydroxy-Phenoxy)

Propionic AcidColumn = (R,R)-ULMO


Hexane/Ethanol+ 0.1% TFA


RebamipideColumn = (S,S)-Whelk-O 2

10/100 25 cm x 4.6 mmMobile Phase: (85/15)

Hexane/Ethanol+ 0.1% TFA

Flow Rate = 2.0 mL/minDetection = UV 220 nmk'1 = 9.64α = 1.21reference 46

NaproxenExtract from Aleve® tablet (99.4%ee)80:20:0.5 hexane/IPA/HOAc2 ml/min; 254 nmRun Time = 10 min4.6 mm x 25 cm (S,S)

Whelk-O 1Sample prep: 1/2 tablet partitioned

between 1M HC1 (2 ml) andCH2C12 (5 ml) with sonication.CH2C12 layer filtered through glasswool and injected

α-Trityl-2-naphthalene propionic acid

Column = (R,R)-ULMO25 cm x 4.6 mm

Mobile Phase =(97/3)Hexane/IPA


CH3

OH

O

O

H3C


Hydratropic Acid CarprofenHydratropic AcidColumn = (R,R)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase: (98/2)Hexane/IPA+ 0.1% Acetic Acid


CarprofenColumn = (R,R)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mmMobile Phase: (85/15)

Hexane/IPA+ 0.1% Acetic Acid


Other Carboxyl ic Acids REGISTetrahydropyrimindine Carboxylic Acid Phenylbutyric acid

Column: (S,S)-ULMO25 cm x 4.6 mmMobile Phase: (90/10)

Heptane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 215 nmRun Time: 14 mink'1 = 3.38α = 1.21reference 48

Column = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)

Heptane/IPA + 0.1% TFAFlow Rate = 2.0 mL/minDetection = UV 215 nmRun Time = 6.5 mink'1 = 3.19α = 1.16reference 48

OH

O

99:1:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 17 min4.6 mm x 25 cm Whelk-O 1k'1 = 4.06α = 1.28reference 18

99:1:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 16 min4.6 mm x 25 cm Whelk-O 1k'1 = 3.45α = 1.38reference 18

k'1 = 3.45

1 38

OH

O

Ph PhPh


Aryl Propionic Acid Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) REGIS

REGIS Other Carboxyl ic Acids

2-Phenylcyclopropane Carboxylate Trolox

1,1'-binaphthyl-2,2'-diylhydrogen phosphateMandelic Acid

OCH3

OOH

CH3

CH3

H3C

HO

Trolox95:5:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 19 min4.6 mm x 25 cm

Whelk-O 1k'1 = 5.09α = 1.21reference 18

OH

O

2-Phenylcyclopropane Carboxylate

99:1 hexane/IPA1 ml/min; 220 nmRun Time = 18 min4.6 mm x 25 cm Whelk-O 1k'1 = 4.19α = 1.34reference 18

56:44 H2O/MeOH, 0.1%HOAc1 ml/min; 254 nmRun Time = 18 min4.6 mm x 25 cm Whelk-O 1k'1 = 4.46α = 1.27

OH

OH

O

Mandelic Acid0.1% HOAc in water1 ml/min; 254 nmRun Time = 13 min4.6 mm x 25 cm Whelk-O 1k'1 = 3.08α = 1.13reference 18

O

O

P

OH

O

Trolox Calcium Channel Blocker

O

CH3

OH

O

CH3

HO

H3C

CH3

Column = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (95/5)

Hexane/IPA +0.1% Acetic acid


Column = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)

Heptane/IPA + 0.1% TFAFlow Rate = 1.0 mL/minDetection = UV 230 nmRun Time = 6 mink'1 = 0.55α = 2.06reference 48

Column = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase = (95/5)

Hexane/IPA + 0.1%Trifluoroacetic Acid






Other Carboxyl ic Acids REGIS











Column = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase: (95/5)



Phenylsuccinic Acid 4-Chloromandelic Acid

Ketorolacα-Methoxyphenyl Acetic Acid

Phenylsuccinic AcidColumn = (S,S)-ULMO



4-Chloromandelic AcidColumn = (R,R)-Whelk-O 2


H2O/CH3OH+ 0.1% Acetic Acid


α-Methoxyphenyl Acetic AcidColumn = (S,S)-Whelk-O 1




KetorolacColumn = (R,R)-Whelk-O 1


Hexane/IPA + 0.1% TFA


Suprofen Ditoluoyltartaric Acid

1-Cyclopentyl-1-phenylacetic AcidTrolox-methylether

Ditoluoyltartaric AcidColumn: (S,S)-ULMO


Hexane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time = 12.0 mink'1 = 2.47α = 1.19reference 48

SuprofenColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase = (80/20) Hexane/IPA +0.01 M Ammonium Acetate


1-Cyclopentyl-1-phenylacetic AcidColumn: (S,S)-ULMO 25 cm

x 4.6 mmMobile Phase: (99/1)


Trolox-methyletherColumn: (S,S)-ULMO




REGIS Other Carboxyl ic Acids

1-Cyclohexyl-1-phenylacetic Acid 2-(2-Chloro-4-methylphenoxy)propionic Acid

2-(3-Chlorophenoxy) Propionic AcidVanilmandelic Acid

1-Cyclohexyl-1-phenylacetic AcidColumn: (S,S)-ULMO 25 cm



2-(2-Chloro-4-methylphenoxy)propionic AcidColumn: (S,S)-ULMO 25 cm x 4.6 mmMobile Phase: (99/1)


Vanilmandelic AcidColumn: (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6Moblie Phase: (85/15)


Flow Rate: 2.0 mL/minDetection: UV 254 nmRun Time: 22.0 mink'1 = 12.34α = 1.27reference 46

2-(3-Chlorophenoxy) Propionic AcidColumn: (R,R)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6Moblie Phase: (99/1)

Hexane/IPAFlow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 17.0 mink'1 = 6.09α = 1.42reference 46


Other Carboxyl ic Acids REGIS4-(Trifluoromethyl)mandelic Acid 2,3-Dibenzoyl-Tartaric Acid

2,3-Dibenzoyl-Tartaric AcidColumn: (R,R)-ULMO

10/100 25 cm x 4.6 mmMobile Phase: (90/10)

Hexane/Ethanol + 10 mM Ammonium Acetate

Flow Rate: 1.5 mL/minDetection: UV 254 nmk'1 = 4.87α = 1.33reference 46

4-(Trifluoromethyl)mandelic AcidColumn: (S,S)-Whelk-O 1

25 cm x 4.6Moblie Phase: (92/8)



Troger’s BaseColumn: (R,R)-Whelk-O 1

(10/100) (FEC) 25 cm x 4.6 mmMobile Phase: (96/4) Hexane/EthanolFlow Rate: 1.5 mL/minDetection: UV 254 nmRun Time = 10.0 mink'1 = 2.52α = 1.80reference 46

N

N

O

Bz

CH3

30% EtOH/hexane1 ml/min; 254 nmrun time = 18 min4.6 mm x 25 cm


Basic Nitrogen REGIS Basic Amine REGIStrans-11,12-Diamino-9,10-dihydro-9,10-ethanoanthracenetrans-11,12-Diamino-9,10-

dihydro-9,10-ethanoanthraceneColumn = ChiroSil® RCA(+)


CH2OH/H2O+ 0.1% Phosphoric acid


Methyl Mandelate 2-Methyl-1-Indanone

OH

O

O

CH3

Methyl Mandelate73:27:0.1 H2O/CH3CN/HOAc1 ml/min; 254 nmRun Time = 20 min4.6 mm x 25 cm Whelk-O 1k'1 = 5.27α = 1.15reference 18

O

CH3

2-Methyl-1-Indanone99:1 hexane/IPA1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm Whelk-O 1k'1 = 4.00α = 1.12reference 18

95:5:0.5 hexane/IPA/HOAc1 ml/min; 280 nm4.6 mm x 25 cm Whelk-O 1k'1 = 1.27α = 1.28reference 26

O

CH3

OEt

O95:5:0.5 hexane/IPA/HOAc1 ml/min; 280 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.75α = 2.53reference 26

O

CH3

OEt

O


O

O

O93:7:0.1 hexane/IPA/HOAc1 ml/min; 254 nmrun time = 30 min4.6 mm x 25 cm Whelk-O 1k'1 = 8.10α = 1.21reference 18

20% IPA/hex2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 5.66α = 1.29reference 7

90:10 hexane/IPA1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.41α = 1.81reference 7


REGIS Esters , Lactones, Ketones, Anhydrides

O

CH3

OH

O

H3C

O

H3CO

O

O


Esters , Lactones, Ketones, Anhydrides REGIS3-Methyl-1-Indanone DPHB

O

CH3

3-Methyl-1-Indanonek'1 = 6.11α = 1.1899:1 hexane/IPA1 ml/min; 254 nmRun Time = 20 min4.6 mm x 25 cm Whelk-O 1reference 18

O

OH

DPHB6% EtOH/hexane1 ml/min; 254 nmRun Time = 41 min4.6 mm x 25 cm Whelk-O 1reference 29

H3C

O


Column = L-Leucine25 cm x 4.6 mmMobile Phase = (99.5/0.5)


O

S

98:2 hexane/IPA1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 7.82α = 1.12reference 7

OOO

EtOO

H

H

O

OEtO

MeOH/IPA/hexane1 ml/min; 254 nmRun Time = 17 min4.6 mm x 25 cm Whelk-O 1k'1 = 12.73α = 1.16reference 19

10% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm


H3CO

O

OCH3

O

97:3 hexane/IPA1 ml/min; 254 nmRun Time = 27 min4.6 mm x 25 cm Whelk-O 1k'1 = 8.46α = 1.08reference 18 OO

2-Methyl-1-Tetralone Diperodon

1,3,5-Triphenylpent-4-yn-1-one

O

CH3

2-Methyl-1-Tetralone99:1 hexane/IPA1 ml/min; 254 nmRun Time = 12 min4.6 mm x 25 cm Whelk-O 1k'1 = 2.76α = 1.11reference 18

DiperodonColumn = (R)-α-Burke 2 25 cm x 4.6 mmMobile Phase = (48/48/4) CH2Cl2/Hexane/Ethanol

+ 1.5 mM Ammonium AcetateFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 9.0 mink'1 = 1.7α = 1.25reference 46

1,3,5-Triphenylpent-4-yn-1-oneColumn = (S,S)-ULMO

25 cm x 4.6 mmMobile Phase =

Hexane + 0.5% IPA


Column = (S,S)-Whelk-O 1


(98/2) Hexane/IPA

Flow Rate = 1.0 mL/minDetection =

UV 254 nmRun Time = 20.5 mink'1 = 1.62α = 4.18reference 51

OO





(98/2) Hexane/IPA


Column = D-Phenylglycine25 cm x 4.6 mmMobile Phase = 99/1)


Column = (S,S)-β-Gem 125 cm x 4.6 mmMobile Phase = (99.5/0.5)



REGIS Esters , Lactones, Ketones, Anhydrides


Esters , Lactones, Ketones, Anhydrides REGISBuckminsterfullerene-Enone [2+2] Photoadducts

Semi-prep separation on analytical column

2:1 toluene/hexane1 ml/min; 400 nmRun Time = 22 minSample: 100µ1 of

5 mg/ml solution (0.5 mg)4.6 mm x 25 cm Whelk-O 1reference 8

Tert-butyl-2-(benzamido) cyclopentyl carbamateTert-butyl-2-(benzamido)

cyclopentyl carbamateColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase = (95/5)Hexane/IPA


1’-Acetoxychavicol Acetate1’-Acetoxychavicol AcetateColumn = (R,R)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm



Ethyl-2-(p-Hydroxyphenoxy) PropionateEthyl-2-(p-Hydroxyphenoxy)

PropionateColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase = (98/2)Hexane/Ethanol



REGIS Amides, Imides, Carbamates , e tc .

EEDQ

BOC-Ala

CBZ-Val

CBZ-Phe

CBZ nornicotine

N O

O O

EEDQ90:10 hexane/IPA1 ml/min; 254 nmRun Time = 25 min4.6 mm x 25 cm


k'1 = 1.75

NO

N

O

Omethanol2 ml/min; 254 nmRun Time = 6 min4.6 mm x 25 cm


CBZ nornicotine

N

N

O O

CBZ nornicotine1:3 MeOH/dichloromethane1 ml/min; 254 nmRun Time = 5 min4.6 mm x 25 cm


O N

O

H

OH

O

CBZ-Phe95:5:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 40 min4.6 mm x 25 cm Whelk-O 1k'1 = 10.2α = 1.20reference 18

O N

O

H

OH

O

CBZ-Val95:5:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 19 min4.6 mm x 25 cm


O N

O

H

CH3

OH

O

BOC-Ala98:2:0.2 hexane/IPA/HOAc1 ml/min; 220 nmRun Time = 17 min4.6 mm x 25 cm Whelk-O 1k'1 = 4.43α = 1.09reference 18

15% EtOH/hexane1 ml/min; 254 nmRun Time = 16 min4.6 mm x 25 cm


ON

O

O

H

80:20:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 25 min4.6 mm x 25 cm

Whelk-O 1k'1 = 5.97α = 1.36reference 18 N

O

OH

Ph

Ph


Amides, Imides, Carbamates , e tc . REGIS

CH3

NH

O

H

ethyl acetate1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.50α = 1.56reference 7

CH3

NH

O

CH3


CH3

NH

O


CH3

N

O

2%EtOH/hex1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 5.13α = 1.03reference 26

ethyl acetate1 ml/min; 254 nm4.6 mm x 25 cm


N OH

Me Et


20% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 4.45α = 1.34reference 26

Np-Ts


Np-Ts

k'1 = 0.14

α = 3.21

CH3

NH

O

N

CH3

H

CH3

O20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 3.72α = 3.17reference 38

N

CH3

H

O

Cl

20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 1.48α = 11.6reference 38

N

CH3

H

CH3

O

I


N

CH3

H

O

Br


N

CH3

H

O

Br


N

CH3

H

O20% IPA/hexane2 ml/min; 254 nmRun Time = 4 min(S,S) Whelk-O 1k'1 = 1.39α = 6.74reference 38


N

CH3

H

O

F


P

NH

O

OEt

OEtH3C

CH3




Amides, Imides, Carbamates , e tc . REGIS

P

NH

O

OEt

OEtH3C

CH3

F


P

NH

O

OEt

OEtH3C

CH3

Cl


P

NH

O

OEt

OEtH3C

CH3

Br


N

H

O

Br

Br

D

H

H

H

H

D

D D

10% acetonitrile in CO2

(S,S) Whelk-O 1k'1 = 19.7α = 1.025reference 39

N

H

O

H

D

D

H

H

H

H

D

D D


(S,S) Whelk-O 1k'1 = 8.5α = 1.025reference 39

N

H

O

D

H

H

H

H

D

D D

TMS

TMS


(S,S) Whelk-O 1k'1 = 25α = 1.025reference 39

Column = (R,R)-Whelk-O 125 cm x 4.6 mm

Mobile Phase = (80/20)Hexane/IPA Flow Rate = 2.0mL/minDetection = UV 254nmRun Time = 19.0 mink'1 = 7.53α = 1.77reference 52

Column = (S,S)-Whelk-O 125 cm x 4.6 mm





REGIS Epoxides

Styrene Oxide Stilbene Oxide

m-Cl Styrene Oxide

OStyrene Oxide1% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm


O

Stilbene Oxide10% IPA/hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.45α = 2.00reference 18

O

0.1% HOAc in hexane1 ml/min; 254 nmRun Time = 20 min4.6 mm x 25 cm Whelk-O 1k'1 = 5.92α = 1.12reference 18

OCl

m-Cl Styrene Oxidehexane1 ml/min; 220 nm4.6 mm x 25 cm

Whelk-O 1reference 30

β-Lactam Cyclopentyl Benzoyl-Diamideβ-LactamColumn: (S,S)-

DACH-DNB25 cm x 4.6 mmMobile Phase: (48/48/2)

Hex/CH2Cl2/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 14.0 mink’1: 3.40α: 1.33reference 59

Cyclopentyl Benzoyl-DiamideColumn: (S,S)-ULMO


Hexane/IPAFlow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 8.7 mink’1: 2.62α: 1.47reference 46

Alcohols REGIS


Ibuprofenol 1,2,3,4-Tetrahydro-1-Naphtol

9-Anthryl Trifluoromethyl Carbinol

α-Naphthyl Methyl Carbinol

Acenaphthenol

Tert Butyl Phenyl Carbinol

CH3

OH

Ibuprofenol99:1 hexane/IPA1 ml/min; 254 nmRun Time = 14 min4.6 mm x 25 cm Whelk-O 1k'1 = 3.38α = 1.05reference 26

OH

1,2,3,4-Tetrahydro-1-NaphtolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)


Tert Butyl Phenyl CarbinolColumn = (S,S)-ULMO


Heptane/IPA Flow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 6.0 mink'1 = 4.60α = 1.46reference 46

CH3

OH

α-Naphthyl Methyl CarbinolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)


9-Anthryl TrifluoromethylCarbinol


Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 10 mink'1 = 1.36α = 2.02reference 46

HO CF3

AcenaphthenolColumn: (R,R)-ULMO25 cm x 4.6 mmMobile Phase: (95/5)

Hexane/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 10 mink’1: 1.68α: 1.46reference 46

OH



H3COH

80:20 hexane/IPA1 ml/min; 254 nmrun time = 10 min4.6 mm x 25 cm


OH

Beta Naphthyl Methyl Carbinol 1,1’-Bi-2-Naphthol

1-Naphthyl-2-butanol

9-Anthrylethanol

2-Naphthyl-2-butanol

Tetrahydrobenzopyrene-7-ol

1,1’-Bi-2-NaphtholColumn = (S,S)-ULMO



9-AnthrylethanolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (95/5) Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 12 mink'1 = 1.82α = 1.74reference 48

2-Naphthyl-2-butanolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (95/5)



Hexane/IPA Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 18.5 mink'1 = 5.59α = 1.09reference 55

CH3

OH

Beta Naphthyl Methyl CarbinolColumn: (R,R)-ULMO25 cm x 4.6 mmMobile Phase: (97/3) Hexane/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 9 mink’1: 1.64α: 1.34reference 46

OH

Tetrahydrobenzopyrene-7-ol80:20 hexane/IPA1 ml/min; 254 nmrun time = 22 min4.6 mm x 25 cm


1-Naphthyl-2-butanolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (95/5)


CH3

OH



REGIS Alcohols


Alcohols REGIS 1-Phenylpentanol Phenyl Tribromomethyl Carbinol

Phenyl Propyl Carbinol

Phenyl Ethyl Carbinol

1,1,2,-Triphenyl-1,2-Ethanediol

Phenyl Methyl Carbinol

1-PhenylpentanolColumn = (S,S)-ULMO


n-Heptane/1,2-Dimethoxyethane


CBr3

OHPhenyl Tribromomethyl CarbinolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)


CH3

OH

Phenyl Methyl CarbinolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = 100%

HexaneFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 14 mink'1 = 3.11α = 1.30reference 46

OH

Phenyl Ethyl CarbinolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)


Phenyl Propyl CarbinolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = 100% HexaneFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 12 mink'1 = 2.25α = 1.56reference 46

OH

1,1,2,-Triphenyl-1,2-EthanediolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)


OHColumn = (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase = (80/20)

Hexane/IPA Flow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 24.0 mink'1 = 13.30α = 1.11reference 55




REGIS Alcohols

1,1’-Binaphthol Monomethylether Terfenadine

2-Methoxyphenyl Phenyl Carbinol

Trans Phenyl Cyclohexanol Analytical vs. Preparative Run

Phenyl cyclohexyl carbinol

Propafenone

Phenyl phenylethyl carbinolPhenyl isopropyl carbinol

1,1'-BinaphtholMonomethyletherColumn: (S,S)-ULMO 25 cm



TerfenadineColumn = (R,R)-Whelk-O 1




PropafenoneColumn = (R,R)-Whelk-O 1


CH2Cl2/Hexane/Ethanol + 0.01 M Ammonium Acetate


Trans Phenyl CyclohexanolAnalytical vs. Preparative Run

Column = (S,S)-ULMO 25 cm x 4.6 mmMobile Phase = (99/1)

Heptane/IPA Flow Rate = 1.0 mL/minDetection = UV 270 nmRun Time = 7.0 minreference 48

2-Methoxyphenyl Phenyl CarbinolColumn = (S,S)-ULMO


Heptane/IPA Flow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 12.0 mink'1 = 2.92α = 1.13reference 48

Phenyl cyclohexyl carbinolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase: (99/1)

Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 6.5 mink'1 = 0.97α = 1.39reference 48

Phenyl isopropyl carbinolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)

Heptane/IPAFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Time: 6 mink'1 = 0.86α = 1.38reference 48

Phenyl phenylethyl carbinolColumn = (S,S)-ULMO25 cm x 4.6 mmMobile Phase = (99/1)

Heptane/IPAFlow Rate = 1.0 mL/min Detection = UV 215 nmRun Time = 9.5 mink'1 = 1.81α = 1.30reference 48

2.8 MG

1.4 MG

0.14 MG


Alcohols REGIS Methyl 3-phenyl-3azido-2hydroxypropanoate

(Erythro-diastereomer)1-(4-Methoxyphenyl)-2-butanol

2-Thiopheneethanol

1-Phenyl-2-propanol

3-Thiopheneethanol

1-(4-Methoxyphenyl)-2-propanol

1-(o-Methoxyphenyl) Ethanol1-(4-Hydroxyphenyl) Ethanol

1-(4-Methoxyphenyl)-2-butanolColumn = (S,S)-ULMO

25 cm x 4.6 mmMobile Phase = (98.5/1.5)



1-Phenyl-2-propanolColumn = (S,S)-ULMO




3-Thiopheneethanol Column = (S,S)-ULMO




1-(o-Methoxyphenyl) EthanolColumn = (S,S)-ULMO




Methyl 3-phenyl-3azido-2hydroxypropanoate(Erythro-diastereomer)

Column = (S,S)-ULMO 25 cm x 4.6 mmMobile Phase = (97/3)

Heptane/GlymeFlow Rate = 1.0 mL/minDetection = UV 215 nmRun Tim = 10.5 mink'1 = 2.34α = 1.16reference 48

1-(4-Methoxyphenyl)-2-propanolColumn = (S,S)-ULMO




2-Thiopheneethanol Column = (S,S)-ULMO




1-(4-Hydroxyphenyl) EthanolColumn = (S,S)-ULMO


n-Heptane/IPA + 0.1% TFAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 8.5 mink'1 = 1.491α = 1.16reference 60


REGIS Alcohols

1-[(4-Phenyl) phenyl] Ethanol 1-(4-Benzyloxy) phenyl Ethanol

1-(m-Trifluoromethylphenyl) Ethanol

1-(p-Flurorophenyl) Ethanol

1-(p-Methylphenyl) Ethanol

1-(p-Bromophenyl) Ethanol

1-(o-Methylphenyl) Ethanol1-(m-Methylphenyl) Ethanol

1-(4-Benzyloxy) phenyl EthanolColumn = (S,S)-ULMO




1-(p-Flurorophenyl) EthanolColumn = (S,S)-ULMO




1-(p-Methylphenyl) EthanolColumn = (S,S)-ULMO




1-(o-Methylphenyl) EthanolColumn = (S,S)-ULMO




1-[(4-Phenyl) phenyl] EthanolColumn = (S,S)-ULMO




1-(p-Bromophenyl) EthanolColumn = (S,S)-ULMO




1-(m-Trifluoromethylphenyl) EthanolColumn = (S,S)-ULMO




1-(m-Methylphenyl) EthanolColumn = (S,S)-ULMO





Alcohols REGIS 1-(o-Chlorophenyl) Ethanol 1-(p-Chlorophenyl) Ethanol

1-(m-Chlorophenyl) Ethanol

1-(p-Chlorophenyl) EthanolColumn = (S,S)-ULMO




1-(o-Chlorophenyl) EthanolColumn = (S,S)-ULMO




RanolazineRanolazineColumn = (R,R)-Whelk-O 1


Hexane/IPA + 35 mMAmmonium Acetate


1-(m-Chlorophenyl) EthanolColumn = (S,S)-ULMO




Phenylethylene GlycolPhenylethylene GlycolColumn = (S,S)-Whelk-O 1


Hexane/EthanolFlow Rate = 2.0 mL/minDetection = UV 254 nmRun Time = 18.7 mink'1 = 11.62α = 1.11reference 46

Benzoin


Hydrobenzoin

Ipsdienol

Anisoin

O

OH

Benzoin80:20:0.5 hexane/IPA/HOAc1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 0.86α = 1.97reference 7

O

OHH3CO

OCH3Anisoin80:20:0.5hexane/IPA/HOAc1 ml/min; 254 nm4.6 mm x 25 cm


60:40 hexane/EtOH1 ml/min; 240 nm4.6 mm x 25 cm Whelk-O 1k'1 = 2.03α = 1.32reference 26

OH

OH

Hydrobenzoin95:5 hexane/IPA1 ml/min; 254 nmRun Time = 18 min4.6 mm x 25 cm Whelk-O 1k'1 = 1.14α = 1.40reference 18

OH

OH

98:2:0.5 hexane/EtOH/HOAc1 ml/min; 240 nm4.6 mm x 25 cm Whelk-O 1k'1 = 4.20α = 1.28reference 26

Ipsdienol2% IPA/hexane1 ml/min; 254 nmRun Time = 8 min4.6 mm x 25 cm


HO

OH

OH


REGIS Diols , Hydroxyketones, e tc .

OH

OHH3CO

OCH3


Sulfoxides REGIS

SCH3

OOH3C

7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmRun Time = 9 min4.6 mm x 25 cm


SCH3

O7:2:1 hexane/IPA/CH2C121 ml/min; 254 nm4.6 mm x 25 cm


SCH3

O

Br

7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmRun Time = 8 min4.6 mm x 25 cm Whelk-O 1k'1 = 3.75α = 1.13reference 18

H3C

S

O

CH3

80:20 hexane/IPA1.5 ml/min; 254 nmRun Time = 14 min4.6 mm x 25 cm Whelk-O 1k'1 = 2.11α = 1.70reference 31

SCH3

O

Br



S

O

CH3





S S O

7:2:1 hexane/IPA/CH2C121 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.29α = 2.14reference 7

SCH3

O


REGIS Sulfoxides

k'1 = 10.72

S

O

O

SCH3

O

7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmrun time = 11 min4.6 mm x 25 cm


7:2:1 hexane/IPA/CH2C122 ml/min; 254 nmrun time = 6 min4.6 mm x 25 cm


Column: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (27.5/27.5/45)

CH2Cl2/Dioxane/HexFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 35.0 mink’1: 10.30α: 1.15reference 59

Column: (R,R)-DACH-DNB25 cm x 4.6 mmMobile Phase:

(98/2) CH2Cl2/IPA

Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 16.0 mink’1: 2.34α: 2.07reference 59

Column: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (98/2)

CH2Cl2/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 13.0 mink’1: 3.08α: 1.26reference 59

Column: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase:

(98/2) CH2Cl2/IPA


OmeprazoleSulfinpyrazoneOmeprazoleColumn = (S)-α-Burke 2 25 cm x 4.6 mmMobile Phase = (95/5) CH2Cl2/CH3OHFlow Rate = 1.0 mL/minDetection = UV 302 nmRun Time = 8.0 mink'1 = 0.64α = 3.04reference 46

SulfinpyrazoneColumn = (R,R)-Whelk-O 1 25 cm x 4.6 mmMobile Phase = (75/25) Hexane/Ethanol

+ 15 mM Ammonium AcetateFlow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 11.0 mink'1 = 3.74α = 1.35reference 46


Sulfoxides REGIS

Column: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (40/40/20)


Column: (R,R)-DACH-DNB25 cm x 4.6 mmMobile Phase: (27.5/27.5/45)


Column: (R,R)-DACH-DNB

25 cm x 4.6 mmMobile Phase:

(27.5/27.5/45) CH2Cl2/Dioxane/Hex


Column: (R,R)-DACH-DNB



PantoprazolePantoprazoleColumn = (R)-α-Burke 2


CH2Cl2/Hexane/Ethanol + 4 mM Ammonium Acetate



REGIS Phosphorous Compounds

P

N

O

OEt

OEt

H

H3CO

5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.26α = 1.50reference 40

P

N

O

OEt

OEt

H

F3CO5% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.72α = 1.26reference 40

P

N

O

OEt

OEt

H


P

N

O

OEt

OEt

H

OCF35% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 6.05α = 1.63reference 40

P

N

O

OEt

OEt

H

OCF35% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 4.10α = 2.08reference 40

P

N

O

OEt

OEt

H

F

F



P

N

O

OEt

OEt

H


P

N

O

OEt

OEt

H


Phosphorous Compounds REGIS

Cyclophosphamide Tertiary Phosphine Oxide

Secondary Phosphine OxidePhosphine Selenium Oxide

P

N

O

OEt

OEt

H


5:4:1 hexane/CH2C12/CH3CN1 ml/min; 254 nm4.6 mm x 25 cm


Tertiary Phosphine OxideColumn: (R,R)-DACH-DNB25 cm x 4.6 mmMobile Phase:

(37.5/37.5/25) Hex/Dioxane/IPA

Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 14.0 mink'1: 2.19α: 1.48reference 59

Secondary Phosphine OxideColumn: (S,S)-DACH-DNB 25 cm x 4.6 mmMobile Phase: (75/25) CH2Cl2/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 19.0 mink'1: 1.49α: 4.11reference 59

P

N

O

OEt

OEt

H


P

N

O

OEt

OEt

H

N


CyclophosphamideColumn = (S,S)-Whelk-O 1



Phosphine Selenium OxideColumn: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (70/30)

Hex/CH2Cl2Flow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 13.0 mink'1: 2.49α: 1.48reference 59


Secondary Phosphine Oxide Tertiary Phosphine Oxide

Tertiary Phosphine OxideSecondary Phosphine Oxide

Tertiary Phosphine OxideColumn: (R,R)-DACH-DNB25 cm x 4.6 mmMobile Phase:

(42.5/42.5/15) Hex/Dioxane/IPA


Tertiary Phosphine OxideColumn:

(R,R)-DACH-DNB25 cm x 4.6 mmMobile Phase: (40/40/20)

Hex/Dioxane/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 14.0 mink’1: 4.19α: 1.25reference 59



P

OH

O

OCH3

OCH3

Secondary Phosphine OxideColumn: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (90/10)

CH2Cl2/IPAFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 8.0 mink'1: 1.23α: 1.81reference 59

Secondary Phosphine OxideColumn: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase:

(90/10) CH2Cl2/IPA



N

N

PO

H

EtOEtO

P

OH

O

OCH3

OCH3



REGIS Phosphorous Compounds


Atropisomers REGIS

CH3

O NEt

EtEtOAc1 ml/min; 254 nm4.6 mm x 25 cm


O

O



CH3

CH3

N

SO

CH3


CH3

O N

80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O-1k'1 = 3.23α = 2.66reference 10

N

SS

CH3


CH3

O N

80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.29α = 2.46reference 10

CH3

O N

80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O-1k'1 = 6.24α = 2.63reference 10 CH3

O N

80:20:0.1%hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O-1k'1 = 4.46α = 2.08reference 10


REGIS Atropisomers


NO

O

NO

O20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 13.00α = 2.57reference 41

NO


NO


NO


NO



NO

O

Cl

Cl


NO

O


Atropisomers REGIS

sulfoxide atropisomer

sulfone atropisomersulfone atropisomer

CH3

O N

CH3

mixture of stereoisomers80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1reference 10

80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1(S)(-) retained on (S,S) CSPk'1 = 1.71α = 3.09reference 10

CH3

O N

sulfoxide atropisomerZ diastereomer2% MeOH in CH2Cl22 ml/min; 300 nm, -40o C4.6 mm x 25 cm Whelk-O 1k'1 = 1.32α = 4.06reference 21

CH3

SO

sulfone atropisomer-80°Creference 22

CH3

SO

H3C

SO

CH3

O N

O


CH3

O N


80:20:0.1% hexane/IPA/HOAc2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 5.11α = 2.04reference 10 CH3

O N

CH3

S OO

sulfone atropisomer2% MeOH in CH2Cl22 ml/min; 300 nm, -80°C4.6 mm x 25 cm Whelk-O 1k'1 = 0.54α = 5.79reference 21


REGIS Atropisomers

NS

O

20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 3.06α = 2.48reference 41 N

S

O

HO


NS

O

Br


NS

O

MeO


NS


NS

OCl


20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.78α = 1.90reference 41N

S

O


NS

O

NO


NO

S20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O CSPk'1 = 6.94α = 1.36reference 41

NO

S20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 6.65α = 1.35reference 41

NO


NO


NO



NO

S20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 5.65α = 1.64reference 41 N

S

O


Atropisomers REGIS


REGIS Atropisomers

NS

S


S

O

Cl


NS

S

HO


NS

S


NS

S


NS

S


15% IPA/hexane1 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.86α = 1.86reference 42

N

N

O

S


N

N

O

S

O2N


Atropisomers REGIS

NS

OCl


S


NS

S


NS

S

HO


NS

S

HO


NS

S

Br


20% 2-propanol in hexane2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.29α = 1.80reference 41N

S

S

Cl


S

S


REGIS Atropisomers

Amlodipine Vapol

Adam’s Acid DiethylamideNimodipine

AmlodipineColumn = (R,R)-

Whelk-O 125 cm x 4.6 mm

Mobile Phase = (46/46/8)CH2Cl2/Hexane/Ethanol +0.01 M Ammonium Acetate


OH

OH

Ph

Ph

VapolColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase =

100% MethanolFlow Rate = 1.5 mL/minDetection = UV 254 nmRun Time = 13 mink'1 = 1.74α = 3.37reference 48

NimodipineColumn = (R,R)-Whelk-O 1


(65/35)Methanol/H2O


Adam’s Acid DiethylamideColumn = (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase = (70/30)



N

N

O

N

F

N

NH2

O

O


NS

S

Phototrigger 1 Phototrigger 2

Phototrigger 3

MesogensPhototrigger 4

O

H H

Phototrigger 18% IPA in hexane1 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1reference 24

O

H3C CH3


O

H3C CH3

O

N

H

H3C

H3C


O

O

CN

O

O

O

CN

MesogensSchuster's candidate photoresolvable mesogensepoxide derivatives reference 13


Optical Switches, Liquid Crystal Components , e tc . REGIS



REGIS Allenes

95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.74α = 2.38reference 42

H

•

CH3

O

O

Cl

H

•

CH3

O

O

F95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 0.72α = 2.33reference 42

H

•

CH3

O

O

O2N


H

•

CH3

O

O


H

•

CH3

O

O


H

•

CH3

O

O



H

•

CH3

O

OH


H

•

CH3

O

OH


H

•

CH3

O

O



H

•

CH3

O

O


H

•

CH3

O

O

O


H

•

CH3

O

O

Br

H

•

CH3

O

O


H CH3

H

•

CH3

O

O



H

•

CH3

O

O

H

•

CH3

O

O

I


Allenes REGIS

REGIS Allenes


H

•

CH3

O

OH

O2N95:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1k'1 = 2.94α = 1.74reference 42

H

•

CH3

O

N

CH3

CH3


H

•

CH3

O

N

H

CH3


H

•

CH3

O

N


H

•

CH3

O

N


H

•

CH3

O

N

H



H

•

CH3

O

N


H

•

CH3

O

N

H

•

CH3

O

OH



H

•

CH3

O

OH

H3CO


H

•

CH3

O

OH

Br

k'1 = 0.90α = 2.5795:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1reference 42

H

•

CH3

O

OH

F

H

•

CH3

O

OH


H

•

CH3

O

OH



H

•

CH3

O

OH

I

H

•

CH3

O

OH

Cl

k'1 = 0.92α = 2.6795:5:1 hexane2-propanol, acetic acid2 ml/min; 254 nm(S,S) Whelk-O 1reference 42


Allenes REGIS

REGIS Allenes


H

•

CH3

O

N

H



H

•

CH3

O

N


H

•

CH3

O

N

H

•

CH3

O

N


H

•

CH3

O

N

H



H

•

CH3

O

N

CH3

H

•

CH3

O

N



Organometal l ic Compounds REGIS

(OC)3Cr O

H3CO

20% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.82α = 1.07reference 20

(OC)3Cr O

H3CO


(OC)3Cr O

CH3


k'1 = 1.71

(OC)3Cr

NH

O


k'1 = 6.79

(OC)3Cr

N

OCH3


(OC)3Cr O



(OC)3CrCH3

NH

O CH3


k'1 = 2.44

(OC)3CrCH3

NH

O

REGIS Organometal l ic Compounds


k'1 = 1.79

α 1 99

(OC)3CrCH3

NH

O


(OC)3CrCH3

NH

O


k'1 = 1.14

(OC)3Cr

NH

O


k'1 = 11.86

(OC)3Cr

N

O CH3


k'1 = 1.86

(OC)3CrOEt

NH

O


k'1 = 3.71

(OC)3Cr

N

O



(OC)3Cr

N

O


k'1 = 2.29

(OC)3Cr

N

O

H

O

CH3

(OC)3Cr

30% CH2Cl2 in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 4.28α = 1.07reference 20

H

O

OCH3

(OC)3Cr


CH3

O

CH3

(OC)3Cr


(OC)3Cr O


OH

CH3

(OC)3Cr


OH

OCH3

(OC)3Cr



Organometal l ic Compounds REGIS

REGIS Agricul tural Compounds


PPO Inhibitor PPO Inhibitor

Tetramethrin

PPO Inhibitor

Bromacil

PPO Inhibitor

Mecoprop MethylPermethrin

O2N

O

O

N N

Et

O NH

CH3

Cl

CF3

PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm


O2N

O

O

N N

CH3

O NH

CH3

Cl

CF3



O2N

O

O

N N

CH3

O NH

H

Cl

CF3



O2N

N

O

N N

CH3

O NH

CH3

Cl

CF3

H



Tetramethrin (insecticide)2% IPA/hexane1 ml/min; 254 nmRun Time = 22 min4.6 mm x 25 cm


O

O

N

O

O

Bromacil (insecticide)2% IPA/hexane1 ml/min; 254 nmRun Time = 38 min4.6 mm x 25 cm


N

NH3C

Br

O

H

O

Cl

Cl

O

O

O

Permethrin (insecticide)0.2% IPA/hexane1 ml/min; 254 nmRun Time = 16 min4.6 mm x 25 cm

Whelk-O 1k'1 = 4.83 cis; 7.46 transα = 1.11 cis; 1.24 transreference 43

O

CH3

O

OCH3

Cl

CH3

Mecoprop Methyl (insecticide)hexane1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm



Agricul tural Compounds REGISResmethrin Metalaxyl

Sethoxydim

Metolachlor

Chrysanthemic Acid-Ethyl Ester

Leptophos, Phosvel

MecopropOmite

ResmethrinColumn: (R,R)-Whelk-O 1

25 cm x 4.6 mmMobile Phase: 100% HexaneFlow Rate:1.0 mL/minDection: UV 254 nmRun Time: 15.0 mink'1 = 6.30α = 1.19reference 46

N

CH3

CH3

CH3

O

OCH3

O

OCH3

Metalaxyl (herbicide)70:30 hexane/IPA1 ml/min; 254 nmRun Time = 13 min4.6 mm x 25 cm


PO

S

OCH3

Cl

Cl

Br

Leptophos, Phosvel (insecticide)

hexane1 ml/min; 254 nmRun Time = 10 min4.6 mm x 25 cm


N

CH3

CH3

CH3

OCH3

O

Cl

Metolachlor (herbicide)2% IPA/hexane1 ml/min; 254 nmRun Time = 25 min4.6 mm x 25 cm


Sethoxydim (herbicide)2% IPA/hexane1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm


NO

OH

O

S

Chrysanthemic acid ethyl ester(mixture of isomers)hexane1 ml/min; 254 nmRun Time = 10 min4.6 mm x 24 cm


O

O

Et

Omite (acaricide)(mixture of isomers)hexane1 ml/min; 254 nmRun Time = 25 min4.6 mm x 24 cm


O

CH3

OH

OCH3

Cl

Mecoprop (herbicide)99:1:0.1 HEX/IPA/HOAc1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm


O

OS

O

OOmite



Propiconazole, Tilt Devrinol, Napropamide

Diclofop Methyl

Crotoxyphos

Diclofop Methyl

Chlorflurecol Methlyl

PPO InhibitorPPO Inhibitor

Cl

OOCl

N

NN

Propiconazole, Tilt (fungicide)

99:1:0.1 IPA/hexa-ne/HOAc1 ml/min; 254 nmRun Time = 70 min4.6 mm x 25 cm


O

CH3

N

O

Devrinol, Napropamide (herbicide)1:1 IPA/hexane1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm


HO

Cl

O

OCH3

Chlorflurecol Methyl(herbicide)2% IPA/hexane1ml/min; 254 nmRun Time 16 min4.6 mm x 25 cm


Crotoxyphos70:30 hexane/IPA1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm


Diclofop Methyl (herbicide)1% IPA/hexane1 ml/min; 254 nmRun Time = 30 min4.6 mm x 25 cm

Whelk-O 1k'1 = 4.29α = 1.21reference 43 O

Cl

Cl

CH3

O

O

CH3O

Diclofop Methyl (herbicide)hexane1 ml/min; 254 nmRun Time = 30 min4.6 mm x 25 cm


Cl

Cl

CH3

O

O

CH3O

O2N

O

O

N N

CH3

O OCH3

Cl

CF3



O2N

O

O

N N

Et

O OEt

Cl

CF3



cis:trans Cypermethrin PPO Inhibitor

Tetramisole

PPO Inhibitor

Silvex Methyl

PPO Inhibitor

cis:trans CypermethrinColumn = (3R,4S)-Pirkle 1-J


Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 22.0 mink'1 (trans) = 4.59α (trans) = 1.19k'1 (cis) = 6.19α (cis) = 1.18reference 46

O2N

O

O

N N

CH3

O OEt

Cl

CF3

PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 3.2α = 1.08reference 23

O2N

O

O

N N

CH3

O O

Cl

CF3

OCH3

PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 6.1α = 1.08reference 23 O2N

O

O

N N

CH3

O O

Cl

CF3

OEt

PPO inhibitor10% IPA in hexane2 ml/min; 254 nm4.6 mm x 25 cm Whelk-O 1k'1 = 4.2α = 1.10reference 23

TtetramisoleColumn = (R,R)-Whelk-O 1


CH2Cl2/Hexane/Ethanol + 0.01 M Ammonium Acetate


Silvex Methyl (herbicide)

hexane1 ml/min; 254 nmrun time = 15 min4.6 mm x 25 cm


O

CH3

O

OCl

Cl

CH3

Cl

Column = (R,R)-Whelk-O 1

25 cm x 4.6 mmMobile Phase = Hexane Flow Rate = 0.5 mL/minDetection = UV 254 nmRun Time = 15.5 minreference 54


25 cm x 4.6 mmMobile Phase = Hexane Flow Rate = 0.5 mL/minDetection = UV 254 nmRun Time = 18.5 minreference 54


Agricul tural Compounds REGIS



Fluazifop-butyl Haloxyfop-ethoxyethyl

Dinocap

Quizalofop-ethylFenoxaprop-ethyl

Fluazifop-butylColumn: (S,S)-DACH-DNB


Hexane/IPATemperature: 20º CFlow Rate: 1.0 mL/minDetection: UV 254 nmRun Time: 11.5 mink'1 = 2.65α = 1.22reference: 59

Haloxyfop-ethoxyethylColumn: (S,S)-DACH-DNB



Fenoxaprop-ethylColumn: (R,R)-DACH-DNB



FenvalerateFenvalerateColumn: (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mmMobile Phase: (99/1)

Hexane/IPAFlow Rate: 3.0 mL/minDetection: UV 254 nmk'A1= 9.36α(A1,A2)= 2.54k'B1= 16.79α(B1,B2)= 1.14reference 46

Quizalofop-ethylColumn: (R,R)-DACH-DNB



Dinocap (fungicide) - mixture of isomershexane1 ml/min; 254 nmRun Time = 15 min4.6 mm x 25 cm Whelk-O 1reference 43

O2N

NO2

O

O2N NO2

O


Miscel laneous Pharmaceut icals REGISNirvanol Mephenytoin

Cyclothiazide

Oxazepam

Bendroflumethiazide

Thalidomide

N

N O

H

HO

CH3

Nirvanol20% IPA/hexane1 ml/min; 254 nmRun Time = 8 min4.6 mm x 25 cm


N

N O

H

CH3O

CH3

Mephenytoin20% IPA/hexane1 ml/min; 254 nmRun Time = 14 min4.6 mm x 25 cm


N

N

O

H

OO

O

Thalidomide63:37:0.1 H2O/MeOH/HOAc1 ml/min; 254 nmRun Time = 33 min4.6 mm x 25 cm


OxazepamColumn = (R,R)-Whelk-O 1


Hexane/IPA + 0.01 MAmmonium Acetate


CyclothiazideColumn = (S,S)-ULMO


Hexane/IPA + 0.1% Acetic Acid


bendroflumethiazidek'1 = 7.89α = 1.161:1 hexane/IPA1 ml/min; 220 nmrun time = 30 min4.6 mm x 25 cm


N

NSS

H2N

OO

F3C

OOH

H

Column: (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase: (60/40)Ethanol/Hexane + 0.1%TriethylamineFlow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 32.0 mink'1 = 3.78α = 1.66reference 55

Column: (S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase: (80/20)Hexane/IPA Flow Rate: 2.0 mL/minDetection: UV 254 nmRun Time: 32.0 mink'1 = 15.64α = 1.33reference 55

McN 5652 Bupivacaine

Cyclandelate

p-Chloro-Warfarin

Indapamide

Tolperisone

N

SCH3McN 56522% IPA/hex w. 0.2%

diethylamine1 ml/min; 254 nm4.6 mm x 25 cm


NN

O

H

Bupivacaine80:20:0.1 hexane/IPA/TEA1 ml/min; 254 nmRun Time = 7-8 min4.6 mm x 25 cm


H3C

O

CH3

N

Tolperisone99:1:0.1 hexane/IPA/TEA1 ml/min; 254 nmRun Time = 18 min4.6 mm x 25 cm


-chloro-warfarin

1 64

O O

OH

CH3

O

Cl

p-Chloro-Warfarin85:15:0.1 MeOH/H2O/HOAc1 ml/min; 254 nmRun Time = 12 min4.6 mm x 25 cm


Cyclandelate (mixture of isomers)hexane1 ml/min; 254 nmRun Time = 35 min4.6 mm x 25 cm


OH

O

O

Iindapamidek'1 = 2.46α = 1.681:1 hexane/IPA1 ml/min; 220 nmRun Time = 14 min4.6 mm x 25 cm

Whelk-O 1reference 18 N

NH

O

CH3

S

Cl

NH2

OO

Column:(S,S)-Whelk-O 125 cm x 4.6 mmMobile Phase: (60/40)

Ethanol/Hexane + 0.1%Triethylamine


Column = (R,R)-Whelk-O 125 cm x 4.6 mmMobile Phase = (95/5)Hexane/IPA Flow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 25.0 mink'1 = 3.45α = 2.04reference 53


REGIS Miscel laneous Pharmaceut icals


Miscel laneous Pharmaceut icals REGISNicardipine Isradipine (reversed phase)

Hanessian’s Lignan

SC 41930

Tropicamide

Isradipine (normal phase)

U-94863U-100057

nicardipine

k' 6 06

N

H

H3C CH3

O OCH3

OO

NO2

N

H3C

Nicardipine73:27:0.1 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 30 min4.6 mm x 25 cm


N

H

H3C CH3

O OCH3

OO

NO

N

Isradipine (reversed phase)63/37 MeOH/H2O1 ml/min; 254 nmRun Time = 35 min4.6 mm x 25 cm


N

O

N

N

H

H3C CH3

O

O

O

O

H3C

Isradipine (normal phase)98:2:0.5 hexane/IPA/TEA1 ml/min; 254 nmRun Time = 52 min4.6 mm x 25 cm


SC 41930

k'1 = 1.05

H3C

O OCH3

O O

O

HO

HO

SC 4193080:20:0.5 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 6 min4.6 mm x 25 cm


Hanessian's lignanmethanol1 ml/min; 254 nmRun Time = 8 min4.6 mm x 25 cm


O

OO

O

H

H

OCH3

OCH3H3CO

TropicamideColumn: (R,R)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase: (75/25)Hexane/Ethanol

Flow Rate: 1.5 mL/minDetection: UV 254 nmRun Time = 13.9 mink'1 = 4.52α = 1.49reference 46

O O

OH

U-10005765:35 hexane/IPA90 ml/min to 34 min,

then 120 ml/minRun Time = 50 min5.1 cm x 25 cm

Whelk-O 1Sample Load = 1.9 greference 37

N Cl

O

Cl

Cl

U-9486370:30:0.5 hexane/

IPA/HOAC12 ml/min; 254 nm2.1 cm x 25 cm

Whelk-O 1Run Time = 12 minSample Load = 40 mgreference 37


U-94863

ProglumideTemazepam

N Cl

O

Cl

Cl

U-9486340:60:0.5 hexane/IPA/HOAc1 ml/min; 254 nmrun time = 15 min4.6 mm x 25 cm


Column: (S,S)-ULMO25 cm x 4.6 mmMobile Phase: (97/3)

Hexane/IPA +0.1% Acetic acid


N

O

H

N

O

OHO

Proglumide75:25:0.1 hexane/IPA/HOAc1 ml/min; 254 nmrun time = 10 min4.6 mm x 25 cm



N

N

O

H

CH3


N

N

O

H

CH3

N

N

O

H


N

N

O

H

CH3O2N



TroglitazoneTroglitazoneColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase = (90/10)Hexane/IPA + 0.1% Acetic Acid



Miscel laneous Pharmaceut icals REGIS

N

N

O

H

CH3Cl



N

N

O

HCl



N

N

O

H

F



N

N

O

H

Cl

Cl



N

N

O

H

Cl



N

N

O

H

F

Cl



70:30:05 hexane/2-propanol/diethyl amine1 ml/min; 254 nm4.6 mm x 25 cm


N N

N

O

H

CH3


Whelk-O 1k'1 = 2.36α = 1.33reference 44 N N

N

O

H

F



N N

N

O

H


Whelk-O 1k'1 = 1.90α = 1.45reference 44 N N

N

O

H

Cl



H3CO

N

OCH3

O

N

N

40% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1α = 1.34Rs = 2.10reference 45

N

NH

NH

O

H

OCH3

50% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 1.32Rs = 2.10reference 45

N

OH

NH

HO

O O


N

O

NH

HO

O O



NN

O

H

O

NH

Br

45% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 2.17Rs = 2.20reference 45 N

N

O

H

H



NO

CH3

H

H

Cl10% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 1.04Rs = 0.60reference 45

NO

CH3

H3C

H

Br10% IPA/hexane1 ml/min4.6 mm x 25 cm(S,S) Whelk-O 1 α = 1.04Rs = 0.60reference 45

F

O

OCH3


NN

O

O

CH3O

NH

CH3

H2N


F3C N

O

H O

Cl

OCH3

O


Bendroflumethiazide

ThalidomideIndapamide

Bendroflumethiazide Column = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (75/25) Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 18 mink'1 = 2.99α = 1.84reference 46

N

N

SS

H2N

OO OO

F3C

H

H

NN

H

CH3

O

Cl

SNH2

O O

IndapamideColumn = (R,R)-ULMO25 cm x 4.6 mmMobile Phase = (75/25) Hexane/IPAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 16 mink'1 = 3.09α = 1.58reference 46

ThalidomideColumn = (R,R)-ULMO 25 cm x 4.6 mmMobile Phase: (90/10)

Hexane/IPA + 0.1% Acetic acid


Warfarin Chlorthalidone

Flobufen and Flobufen Metabolites

4(3H)-Quinazolone Derivatives

Flobufen Metabolites

4(3H)-Quinazolone Derivatives4(3H)-Quinazolone Derivatives



α = 1.14

α = 1.14 α = 1.14

α = 1.20α = 1.08

WarfarinColumn: (S,S)-ULMO25 cm x 4.6 mmMobile Phase: (70/30)

Heptane/IPA + 0.1% TFAFlow Rate: 1.0 mL/minDetection: UV 230 nmRun Time: 6.5 mink'1 = 0.89α = 1.36reference 48

ChlorthalidoneColumn = (S,S)-DACH-DNB


CH2Cl2/CH3OH + 0.01 M Ammonium Acetate


Flobufen MetabolitesColumn = (S,S)-ULMO 25 cm x 4.6 mmMobile Phase = (97/3)

Heptane/Glyme + 0.1% TFA

Flow Rate = 1.0 mL/minDetection = UV 215 nmRun Time = 21.0 minreference 47

Flobufen and FlobufenMetabolites

Column = (S,S)-ULMO 25 cm x 4.6 mmMobile Phase = (90/10)Heptane/IPA + 0.1% TFA Flow Rate = 2.0 mL/minDetection = UV 230 nmRun Time = 24.0 minreference 47

4(3H)-Quinazolone DerivativesColumn = (S,S)-Whelk-O 1



4(3H)-quinazolonederivatives

Column = (S,S)-Whelk-O 125 cm x 4.6 mm



4(3H)-quinazolone derivativesColumn = (S,S)-




Dexmedetomidine (Enriched)Dexmedetomidine (Enriched)Column = (S,S)-Whelk-O 2


Hexane/Ethanol + 10 mM Ammonium Acetate




Sulpiride

Ketoconazole

Coumachlor

Tofisopam and it’s ConformersTofisopam and it’s ConformersColumn = (R,R)-β-Gem 1


Hexane/Ethanol + 0.1% TEAFlow Rate = 1.0 mL/minDetection = UV 254 nmRun Time = 25.0 mink'1 = 2.66α = 3.13reference 46

4(3H)-Quinazolone Derivatives 4(3H)-Quinazolone Derivatives

KetamineIfenprodil







IfenprodilColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase = (85/15)Hexane/IPA +0.01 M Ammonium Acetate


KetamineColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase = (99/1)Hexane/IPA + 0.1% TEA


KetoconazoleColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase = (46/46/8)CH2Cl2/Hexane/IPA +0.01 M Ammonium Acetate


CoumachlorColumn = (R,R)-Whelk-O 1


Hexane/Ethanol +0.1% Acetic Acid


SulpirideColumn = (R,R)-DACH-DNB


CH2Cl2/Ethanol +0.01 M Ammonium Acetate




Ofloxacin Isoxsuprine

Cromakalim

Warfarin (Reversed Phase)

Trichlormethiazide

Warfarin (Normal Phase)

PrilocaineTemazepam

OfloxacinColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mmMobile Phase = (43/43/14)

CH2Cl2/Hexane/Ethanol +0.01 M Ammonium Acetate


IsoxsuprineColumn = (R,R)-Whelk-O 1




Warfarin (normal phase)Column = (R,R)-


Mobile Phase = (65/35) Hexane/IPA+ 0.1% Acetic Acid


Warfarin (reversed phase)Column = (R,R)-


Mobile Phase = (70/30) CH3OH/H2O+ 0.1% Acetic Acid


CromakalimColumn = (R,R)-Whelk-O 1



TrichlormethiazideColumn = (R,R)-ULMO


(75/25)Hexane/IPA +0.1% Acetic Acid


TemazepamColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase = (80/20) Hexane/IPA + 0.1% Acetic Acid


PrilocaineColumn = (S,S)-ULMO


(99/1) Hexane/Ethanol + 0.01 M Ammonium Acetate



Miscel laneous Pharmaceut icals REGISLorazepam Althiazide

Methadone Hydrochloride

Metolazone

Ethotoin

Clenbuterol

LansoprazoleZopiclone

LorazepamColumn = (R,R)-Whelk-O 1



Flow Rate = 1.5 mL/minDtection - UV 254 nmRun Time = 9.0 mink'1 = 2.08α = 2.02reference 46

AlthiazideColumn = (S,S)-ULMO




ClenbuterolColumn = (R)-α-Burke 2


CH2Cl2/Ethanol +0.01 M AmmoniumAcetate


MetolazoneColumn = (R,R)-




Methadone HydrochlorideColumn = (S)-α-Burke 2


(88/12)Hexane/Ethanol + 0.1% TEA


EthotoinColumn = (S,S)-Whelk-O 1


(75/25)Hexane/Ethanol

Flow Rate = 1.5 mL/minDtection - UV 254 nmRun Time = 11.0 mink'1 = 1.65α = 3.03reference 46

ZopicloneColumn = (R,R)-Whelk-O 1


CH2Cl2/Ethanol + 0.01 M Ammonium Acetate


LansoprazoleColumn = (S)-α-Burke 2


(94/3/3)CH2Cl2/Ethanol/Methanol + 0.2% Acetic AcidFlow Rate = 1.5 mL/min

Detection = UV 254 nmRun Time = 6.0 mink'1 = 0.88α = 2.43reference 46

Chlormezanone Tetrabenazine

trans-U-50488HDihydrotetrabenazine



ChlormezanoneColumn = (R,R)-Whelk-O 1



TetrabenazineColumn = (S,S)-Whelk-O 1

10/100 (FEC)25 cm x 4.6 mm

Mobile Phase = (55/45) Hexane/IPA + 0.1% TFA


DihydrotetrabenazineColumn = (S,S)-Whelk-O 1

10/100 (FEC)25 cm x 4.6 mm

Mobile Phase = (60/40) Hexane/IPA + 0.1% TFA


trans-U-50488HColumn = (3R,4S)-Pirkle I-J




Fluridil Alfuzosin

PazufloxacinDoxazosin

FluridilColumn = (S,S)-Whelk-O 2


(57/43)H2O/CH3OH


AlfuzosinColumn = (R,R)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm

Mobile Phase = (68/28/4)Hexane/CH2Cl2/Ethanol + 4 mM Ammonium Acetate


DoxazosinColumn = (S,S)-Whelk-O 1


Hexane/CH2Cl2/Ethanol + 5 mM Ammonium Acetate


PazufloxacinColumn = (S,S)-Whelk-O 1


CH2Cl2/Hexane/IPA+ 0.15% TFA



Miscel laneous Pharmaceut icals REGISMosapride Modafinil

Lorglumide

Nadifloxacin

Idazoxan

Sulindac

MosaprideColumn = (R,R)-

Whelk-O 110/100 (FEC) 25 cm x 4.6 mm

Mobile Phase = (66/28/6)Hexane/CH2Cl2/Ethanol


ModafinilColumn = (S,S)-Whelk-O 1

10/100 (FEC)25 cm x 4.6 mm



SulindacColumn = (R,R)-Whelk-O 1

10/100 (FEC)25 cm x 4.6 mm

Mobile Phase = (48/48/4)Hexane/CH2Cl2/IPA+ 0.1% Acetic acid


NadifloxacinColumn = (S,S)-Whelk-O 1

10/100 (FEC)25 cm x 4.6 mm

Mobile Phase = (45/45/10)CH2Cl2/Hexane/IPA+ 10 mM Ammonium Acetate


LorglumideColumn = (R,R)-Whelk-O 1

10/100 (FEC)25 cm x 4.6 mm

Mobile Phase = (95/5)Hexane/IPA + 0.1% Acetic Acid


IdazoxanColumn = (S,S)-Whelk-O 1


Hexane/MethyleneChloride/IPA+ 0.1% TEA

Flow Rate = 2.0 mL/minDtection - UV 254 nmk'1 = 5.86α = 1.23reference 46


r-7,t-8-Dihydroxy-t-9, 10-epoxy-7,8,9, 10-tetrahydrobenzo[a]pyrene

r-7,t-8-Dihydroxy-t-9, 10-epoxy-7,8,9, 10-tetrahydrobenzo[a]pyrene

40% EtOH/Hexane4.6 mm x 25 cm (R,R) β-Gem 11 ml/min; 254 nmRun Time = 14 mink'1 = 3.18α = 1.25

O�H�

HO�

O�

1-Naphthylureaphenethylamine30% EtOH/Hexane4.6 mm x 25 cm

D-Phenyglycine1 ml/min; 254 nmRun Time = 10 mink'1 = 2.37α = 1.22

HN� C� N� CH�

CH�3�O� H�

Diol Epoxides REGIS Ureas REGIS1-Naphthylureaphenethylamine

Hexobarbital

N�

N� O�Na�

O�

CH�3�

H�3�C�

Hexobarbital5% EtOH/Hexane0.7 ml/min; 254nmrun time = 16 min4.6 mm x 25 cm

L-Leucinek'1 = 2.89α = 1.10

REGIS Barbi turates


Natural Products REGIS

Calanolide A (semi prep)Calanolide A

Flavanone 2-cis-4-trans-Abscisic Acid (ABA)

Combretastatin D-1

ABA Methyl Ester

Combretastatin D-1

2-trans-4-trans-Abscisic Acid

flavanone

k'1 = 7 08

O

OFlavanone1% IPA/hexane1 ml/min; 254 nmRun Time = 25 min4.6 mm x 25 cm


CH3

OH

CH3H3C

OHO

2-cis-4-trans-Abscisic Acid (ABA)80:20:0.5 hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 5 min4.6 mm x 25 cm


O

CH3

OH

CH3H3C

O

OH

2-trans-4-trans-AbscisicAcid (ABA)80:20:0.5

Hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 5 min4.6 mm x 25 cm


O

CH3

OH

CH3H3C

O

OH

O O

CH3

ABA Methyl Ester80:20:0.5

Hexane/IPA/HOAc1 ml/min; 254 nmRun Time = 5 min4.6 mm x 25 cm


Combretastatin D-120% IPA/Hexane2 ml/min; 254 nmrun time = 13 min4.6 mm x 25 cm


O

OH

O

OO

Combretastatin D-1semi-prep separation20% IPA/hexane2 ml/min; 300 nm200 µl of 12.7 mg/ml solnload = 2.5 mgrun time = 10 min4.6 mm x 25 cm


O

OH

O

OO

O O

O

OH

O

Calanolide A10% IPA/hexane1.25 ml/min; 270 nmrun time = 18 min4.6 mm x 25 cm


O O

O

OH

O

Calanolide A (semi prep)10% IPA/hexane1.25 ml/min; 270 nmrun time = 18 min4.6 mm x 25 cm

Whelk-O 15 mg samplek'1 = 3.2α = 1.4reference 16

Abscisic AcidAbscisic AcidColumn = (R,R)-Whelk-O 1




TetrahydropalmatineTetrahydropalmatineColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mm




REGIS Natural Products

REGIS β−Blockers

LuciferinTaxifolinLuciferinColumn = L-Leucine


Hexane/Ethanol + 0.04 mMAmmonium Acetate


TaxifolinColumn = (S,S)-Whelk-O 2

10/100 (FEC)25 cm x 4.6 mm

Mobile Phase = (85/15)Hexane/Ethanol + 0.1% TFA


β-Blockerβ-blockerColumn: (S,S)-DACH-DNB25 cm x 4.6 mmMobile Phase: (92/8)


BambuterolBambuterolColumn = (R,R)-alpha-Burke 2


Hexane/MethyleneChloride/Ethanol + 20 mMAmmonium Acetate



β−Blockers REGISAlprenolol Betaxolol

Bufuralol

Bupranolol

Metoprolol

Atenolol

β-BlockerTulobuterol HCI

O

OH

N

H

Alprenolol90:5:5 CH2C12/EtOH/MeOH10 mM NH4OAc1 ml/min; 254 nmrun time = 10 min4.6 mm x 25 cm

α-Burke 2k'1 = 1.44α = 1.44reference 33

O

OH

N

H

O

Betaxolol85:10:5 CH2C12/EtOH/MeOH10 mM NH4OAc1 ml/min; 254 nmrun time = 11 min4.6 mm x 25 cm


O

H2N

O

OH

N

H

Atenolol85:10:5CH2C12/EtOH/MeOH15 mM NH4OAc1 ml/min; 254 nmrun time = 16 min4.6 mm x 25 cm


BupranololColumn: (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase: (85/15)

CH2Cl2/Ethanol + 0.015M Ammonium Acetate


BufuralolColumn: (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase: (90/10)

CH2Cl2/Ethanol + 0.02 M AmmoniumAcetate


metoprolol85:10:5 CH2C12/EtOH/MeOH10 mM NH4OAc1 ml/min; 254 nmrun time = 13 min4.6 mm x 25 cm


O

OH

N

H

O

CH3

Tulobuterol HCIColumn: (S)-α-Burke 2


CH2Cl2/Ethanol + 0.01 M Ammonium Acetate


β-BlockerColumn: (S,S)-

DACH-DNB25 cm x 4.6 mmMobile Phase:

(90/10) CH2Cl2/IPA



REGIS β−Blockers

Nadolol Timolol Maleate

Carazolol

NadololColumn = (S,S)-Whelk-O 1




Timolol MaleateColumn = (3R,4S)-Pirkle 1-J


(94/3/3) CH2Cl2/Ethanol/IPA+ 0.01M Ammonium Acetate


CarazololColumn = (R)-α-Burke 2


(46/46/8) CH2Cl2/Methanol/Ethanol + 0.01 MAmmonium Acetate


Practolol

Pronethalol

Practolol85:10:5 CH2C12/

EtOH/MeOH15 mM NH4OAc1 ml/min; 254 nmrun time = 19 min4.6 mm x 25 cm


OH

N

H

Pronethalol90:10 CH2C12/EtOH15 mM NH4OAc1 ml/min; 254 nmrun time = 15 min4.6 mm x 25 cm


Pindolol

Oxprenolol

Propranolol

PindololColumn: (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase: (80/20)



OxprenololColumn: (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase: (90/10)



PropranololColumn: (3R,4S)-Pirkle 1-J25 cm x 4.6 mmMobile Phase: (80/20)



practolol

O

OH

N

H

N

O

H

H3C


Amino Acids REGISNorleucine 4-Fluorophenyalanine

1-Aminoindan

Arginine

Tyrosine

1,2,3,4-Tetrahydro-1-naphthylamine

LeucineMethionine

NorleucineColumn: ChiroSil® RCA(+)

or SCA(-)15 cm x 4.6 mm

Mobile Phase: (45/55) CH3OH/H2O+10 mM Acetic acid

Flow Rate: 1.0 mL/minDetection: UV 210 nmRun Time: 5.6 mink'1: 1.28α: 1.75

4-FluorophenyalanineColumn: ChiroSil® RCA(+) or

SCA(-) 15 cm x 4.6 mmMobile Phase: (70/30)

CH3OH/H2O+10 mM Acetic acid


1,2,3,4-Tetrahydro-1-naphthylamineColumn: ChiroSil® RCA(+)

or SCA(-) 15 cm x 4.6 mmMobile Phase: (84/16)

CH3OH/H2O+10 mM H2SO4 and 0.1% TEA


ArginineColumn: ChiroSil®

RCA(+) or SCA(-)15 cm x 4.6 mm

Mobile Phase: (84/16) CH3OH/H2O+10 mM H2SO4


1-AminoindanColumn: ChiroSil®


Mobile Phase: (84/16)CH3OH/H2O+5 mM HClO4


TyrosineColumn: ChiroSil®




MethionineColumn: ChiroSil® RCA(+)

or SCA(-) 15 cm x 4.6 mm



LeucineColumn: ChiroSil®





REGIS Amino Acids

KynurenineKynurenineColumn = (S,S)-Whelk-O 1

10/100 (FEC) 25 cm x 4.6 mmMobile Phase =

(65/35)H2O/CH3OH + 0.1% Acetic Acid


Serine

Tryptophan

Phenylalanine

NorvalinePhenylglycine

TryptophanColumn: ChiroSil®




SerineColumn: ChiroSil® RCA(+)

or SCA(-)15 cm x 4.6 mm

Mobile Phase: (84/16) CH3OH/H2O+5 mM HClO4


PhenylalanineColumn: ChiroSil® RCA(+) or

SCA(-) 15 cm x 4.6 mmMobile Phase: (70/30)

CH3OH/H2O+10 mM Acetic acid


PhenylglycineColumn: ChiroSil® RCA(+)

or SCA(-)15 cm x 4.6 mmMobile Phase: (70/30)

CH3OH/H2O+10 mM H2SO4 and 0.1% TEA


NorvalineColumn: ChiroSil® RCA(+) or

SCA(-)15 cm x 4.6 mmMobile Phase:

(45/55) CH3OH/H2O+10 mM Acetic acid


D,L-p-Hydroxy-PhenylglycineD,L-p-Hydroxy-PhenylglycineColumn: ChiroSil®-SCA(+)


(50/50) CH3ON/H2O+0.02% Acetic acid


GlutamineGlutamineColumn: ChiroSil® SCA(-)


(65/35) CH3CN/H2O+0.01% Acetic acid



Amino Acids REGISHistidine Glutamic Acid

Lysine

EthionineDOPA

HistidineColumn: ChiroSil®




Glutamic AcidColumn: ChiroSil®


Mobile Phase: (65/35) CH3OH/H2O+0.05% Phosphoric acid


DOPAColumn: ChiroSil®




EthionineColumn: ChiroSil®


Mobile Phase: (75/25) CH3OH/H2O+0.02% Acetic acid


LysineColumn: ChiroSil®




Throughout the past 20 years, the Sales and Technical persons atRegis have fielded hundreds of different questions related to our

Chiral Stationary Phases (CSP’s). Listed here you will find some ofthe frequently asked questions. By no means is this a complete list,if you have questions regarding chiral chromatography, please feelfree to contact Regis directly or pass your question on through oneof our distributors.

What is the pressure rating of your columns?All analytical (25cm x 4.6 mm i.d.) and semi-preparative (25cm x 10.0 mm i.d.) columns manufactured by Regis can tolerate pressures up to 6000 psi. Larger columns will tolerate3000 psi. It is very important not to exceed the maximum pressurerating for any HPLC column as you may disrupt the integrity of thesilica bed and destroy the column.

Can Regis columns be reversed?Yes, all columns packed by Regis are fully reversible. In fact, Regiswas the first column manufacturer to sell a fully reversible HPLC column. It is recommended to reverse your column frequently. Thishelps keep the frit surface from becoming clogged with undissolvedsample or particulates in the mobile phase, thus extending the column life.

What is the pH range of your columns?All of Regis’ Chiral phases are bonded on silica. The recommendedpH range is 2.5 to 7.5. Limited usage outside of this pH range canbe tolerated, but it has been proven that extended usage outside ofthe range will decrease column life.

Can your columns be used in normal and reversed-phase solvents?Yes, all Pirkle-Type Chiral HPLC columns can be used in BOTHnormal and reversed-phase solvents. Generally, the Pirkle-TypeCSP’s will give better separations by using them with normal-phasesolvents. There are numerous examples, however; whereseparations with reversed-phase solvents will outperform those with normal-phase solvents.

Can I use the same column for reversed-phase and normal-phase solvent systems while doing method development?Yes, just make sure you completely flush out the column with a miscible solvent such as IPA or ethanol. We recommend at least 20 column volumes.

How long does it take your columns to equilibrate?The column should equilibrate after about 20 column volumes.When you are switching from normal to reversed-phase solventsystems and vise-versa, flush the column with a miscible solvent for20 column volumes. It should take another 20 column volumes toequilibrate. The equilibration volumes may vary depending on thecomposition of the mobile phase.

What type of silica do you use?Regis exclusively uses Exsil® for our 5-micron material andKromasil‚ for 10 and 16-micron material. Both brands of silica are100 angstrom in pore size.

Do you always need a modifier in the mobile phase?No modifiers are usually needed for initial method development.Modifiers can be used to improve peak shape and resolution whenthe samples are extremely basic or acidic in nature. Acetic acid orammonium acetate are recommended for acidic compounds, andtriethylamine, diethylamine or ammonium acetate arerecommended for basic compounds. Usually 0.1% of modifier is allthat is required. Note: Although TFA may be used as a modifier,its use should be limited. Acetic acid usually works as well as TFA.

Can I use your columns for SMB chromatography and SFC?Yes, many analytical and preparative chromatographers usePirkle-Type Chiral columns in both SFC and SMB. Specialhardware is necessary for certain column dimensions.

What is the difference between Whelk-O 1 and Whelk-O 2?Although the Whelk-O 1 and Whelk-O 2 both share the sameChiral selector, they have distinct differences. The Whelk-O 1 ismonofunctionally bonded to silica and the Whelk-O 2 istrifunctionally bonded. The Whelk-O 2 was designed to toleratestrong acidic modifiers such as TFA. The Whelk-O 2 was designedfor preparative use and is not available on 5-micron silica. Due tothe fact the Whelk-O 2 is a trifunctional bond, coverage on the silicawill be less than with Whelk-O 1. This decrease in the actual numberof bonded sites will decrease selectivity and not allow for exactreproducibility of a method developed on a Whelk-O 1 column.

Does my compound need an aromatic ring to achieve separation on a Pirkle-Type Chiral column?In most cases (not all), yes. Chiral recognition occurs at bindingsites. The potential π-π interaction that can occur between the aromatic rings on the Chiral selector and the aromatic ring on thesample is a major factor in achieving selectivity. Binding doesoccur at other sites such as acidic sites, basic sites and stericinteraction sites—this is why you do not always need a ring—butby far, the π-π interaction is the major binding site.

Can I use the Pirkle-Type Chiral columns in polar organic mode?Yes, even though the success rate is very poor, you can use thecolumns in polar organic mode. We do not recommend dedicatinga slot in your method development station for a Pirkle-Type Chiralcolumn if you are exclusively running in polar organic mode. Addanother Pirkle-Type column to your normal-phase system toachieve a higher success rate.

What sampling loading can I expect from Pirkle-Type ChiralHPLC columns?The typical loading range – with relative retention’s (alpha) greaterthan 1.3—is ~ 4-16 mg of sample per gram of packing. Below aretypical loadings for some of the different column sizes: Note:Factors, such as solubility, will greatly affect loading capacity.Analytical column, 25cm x 4.6mm, ~ 3.5 grams of packing,

loading is 14-56 mg/ injection.Semi-prep column, 25cm x 10.0mm, ~ 16 grams of packing,

loading is 64-256 mg/ injection.Prep column, 25cm x 21.1mm, ~ 72.5 grams of packing,

loading is 288-1,152 mg/ injection.

Frequently Asked QuestionsABOUT PIRKLE-TYPE CHIRAL STATIONARY PHASES AND COLUMNS FROM REGIS


STEP 1: Choosing the Appropriate Column:

We recommend using the following sequence of columns to startyour method development. When doing method development atRegis, the Whelk-O is our first choice as it exhibits the broadestdegree of generality.

Order of Preference:

� Whelk-O

� ULMO

� DACH-DNB

� α-Burke

� β-Gem

� Pirkle 1-J

� Leucine

� Phenylglycine

STEP 2: Choosing the Mobile Phase:

Certain factors such as solubility and future considerations forpreparative work usually help to determine whether to performyou method development with reversed-phase or normal phasesolvents. Pirkle-Type phases can be used in both modes, buttypically performs the best with normal phase solvents. Since themajority of analytical Chiral methods move on to preparativeseparations, we recommend using normal phase solvents.

Typical Mobile Phase Combinations:

� Hexane/IPA � Heptane/IPA

� Hexane/Ethanol � Methanol/H2O

� Hexane/CH2CL2/Ethanol � Ethanol/H2O

� Hexane/Ethyl Acetate � Acetonitrile/H2O

� Heptane/Ethanol � Methanol/CH2CL2

� Heptane/CH2CL2 � THF/H2O

� Hexane/CH2CL2 � Ethanol/CH2CL2

STEP 3: Start with a high percentage (~50%) ofstrong solvent (ethanol, IPA, ect.):

Starting with a strong solvent system ensures that all peaks willelute off the column quickly.

� If you achieve any resolution, (such as the above sample)move on to STEP 4.

� If your sample comes off in the void, decrease the strongsolvent by half.

� If your sample is now out of the void and you haveresolution, move on to STEP 4.

� If your sample is out of the void, and there is no resolution,change the column.

Quick Scheme Method DevelopmentFOR THE REGIS PIRKLE-TYPE CHIRAL STATIONARY PHASES


Steps 4 and 5 continued on pages 84 & 85

Sample: NaproxenColumn: (R,R)-Whelk-O 1


Hexane/EthanolFlow Rate: 1.5 mL/minDetection: UV 254 nmRun Time: 6.5 min


STEP 4: Add a Mobile Phase Modifier (usually ~ 0.1%)

� For this sample, you can stop at 50/50 Hexane/Ethanol + 0.1% acetic acid if you are only looking for a basic methodor you can carry it forward to STEP 5 and optimize.


Recapping The First Four Steps:

As you can see, the peak shape of the initial separation is verypoor. To rectify this problem, a modifier is usually added. If youare satisfied with the peak shape—you do not need to add amodifier—move on to STEP 5 and optimize your separation.

� For basic or amine groups—add triethylamine, diethylamineor ammonium acetate

� For acidic groups—add acetic acid, trifluoroacetic acid orammonium acetate

� Although resolution increased with the addition of 0.1% of triethylamine to the mobile phase, the peak shape is stillvery poor.

� Try adding a different modifier

� Resolution and peak shape are excellent with the addition of0.1% of acetic acid

REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral 85

STEP 5: Optimizing your method:


Optimizing a Chiral method is very similar tooptimizing an achiral method. Changing mobilephase component concentrations and even thecomponents themselves can dramatically changeresolution.

Increase the concentration of the weaker solvent:

� Increasing the hexane content increased the resolution in this example. Again, you can stop here and accept this asoptimized or continue on.

Change the strong solvent:

� By substituting IPA for ethanol, an increase in both resolution and alpha were achieved.

Optimization of a Chiral method can be assimple or as complicated as you want it to be.Different mobile phase components can be used; modifiers can be changed or eliminated;you can switch to reversed-phase solvents; you can change columns. The possibilities areendless. We suggest you keep it as simple as possible. Once you have achieved anacceptable separation, move on to the nextproject. Small increases in resolution and alpha are usually not worth the time spent in method development to achieve thoseincreases.

?Not sure which chiral column to use for your separation?Let the professional staff at Regis assist you with its free chiral screening service.

Simply fill out the chiral screening data sheet (see page 91 of this Guide) and pre-fax it to Regis or send it along with your sample of interest.

STRICTLY CONFIDENTIAL • FAST TURN AROUND TIME • NO OBLIGATION TO THE [email protected]

1. Pirkle, W. H.; Welch, C. J.; Burke, J. A., Lamm, B., Target-directed Design ofChiral Stationary Phases, Analytical Proceedings, 1992, 29, 225.

2. Pirkle, W. H.; Welch, C. J.; Hyun, M. H., Concerning the Role of Face-to-Edge π-π Interactions in Chiral Recognition, J. Chromatogr., 1992, 607, 126.

3. Pirkle, W. H.; Welch, C. J.; Lamm, B., Design, Synthesis, and Evaluation of anImproved Enantioselective Naproxen Selector, J. Org. Chem., 1992, 57, 3854.

4. Pirkle, W. H.; Welch, C. J., An Improved Chiral Stationary Phase for theChromatographic Separation of Underivatized Naproxen Enantiomers, J. Liq.Chromatogr., 1992, 15(11), 1947.

5. Pirkle, W. H.; Welch, C. J.; Wilson, S. R., Assignment of Absolute Configurationto an Improved Enantioselective Naproxen Selector, Chirality, 1994, 6, 615.

6. Welch, C. J., Analytical & Semipreparative Separation of Enantiomers Using theWhelk-O 1 Chiral Stationary Phase: Naproxen & Abscisic Acid as Case Studies,Chemistry in New Zealand, 1993, July, 9.

7. Pirkle, W. H.; Welch, C. J., Use of Simultaneous Face to Face to Edge π-π Interactions to Facilitate Chiral Recognition, Tetrahedron: Asymmetry, 1994, 5, 777.

8. Wilson, S. R.; Wu, Y.; Kaprinidis, N. A.; Schuster, D. I.; Welch, C. J., Resolutionof Enantiomers of C60-Enone Photoadducts: Mirror Image Fullerenes, J. Org.Chem., 1993, 58, 6548.

9. Welch, C. J., An Improved Method for the Direct Chromatographic Resolution ofAbscisic Acid Enantiomers, Chirality, 1993, 5, 569.

10. Pirkle, W. H.; Welch, C. J.; Zych, A. J., Chromatographic Investigation of theSlowly Interconverting Atropisomers of Hindered Naphthamides, J. Chromatogr.,1993, 648,101.

11. Zhen, L.; Conser, K. R.; Jacobsen, E. N., Asymmetric Alkene Aziridination withReadily Available Chiral Diimine-Based Catalysts, J. Amer. Chem. Soc., 1993,115, 5326.

12. Blum, A. M.; Lynam, K. G.; Nicolas, E. C., Use of a New Pirkle-type ChiralStationary Phase in Analytical and Preparative Subcritical Fluid Chromatographyof Pharmaceutical Compounds, Chirality, 1994, 6, 302.

13. Zhang, Y.; Schuster, G. B. A Search for Photoresolvable Mesogens: Synthesis andProperties of a Series of Liquid Crystalline, Axially Chiral 1-Benzylidene-4 -

[4'-[(p - alkylphenyl)ethnyl]phenyl]cyclohexanes, J. Org. Chem., 1994, 59, 1855.14. Pirkle, W. H.; Welch, C. J., Chromtographic and 1H NMR support for a

proposed chiral recognition model, J. Chromatogr., 1994, 683, 347.15. Wan, K. T.; Davis, M. E., Asymmetric Synthesis of Naproxen by Supported

Aqueous-Phase Catalysis, Journal of Catalysis, 1994, 148, 1.16. Cardellina, J.H.; Bokesch, H.R.; McKee, J.C.; Boyd, M.R., Resolution and

Comparative Anti-HIV Evaluation of the Enantiomers of Calanolides A and B,Bioorg & Med. Chem. Lett., 1995, 1011.

17. Rychnovsky, Pettit & Welch, unpublished results.18. Welch, Szczerba & Perrin, Regis Technologies, Inc., unpublished results.19. Pickard, S.T.; Pirkle, W.H.; Tabatabai, M.; Vogt, W.; Boehmer, V., Dissymmetric

Calix[4]arenes: Optical Resolution of Some Conformationally Fixed Derivatives,Chirality, 1993, 5, 310.

20. Villani, C.; Pirkle, W.H., Direct High-Performance Liquid ChromatographicResolution of Planar Chiral Tricarbonyl (h6-arene)-chromium(0) Complexes, J. Chromatogr., 1995, 693, 63.

21. Villani, C.; Pirkle, W.H., Chromatographic Resolution of the InterconvertingStereoisomers of Hindered Sulfinyl and Sulfonyl Naphthalene Derivatives,Tetrahedron: Asymmetry, 1995, 6, 27-30.

22. Casarini, D.; Lunazzi, L.; Alcaro, S.; Gasparrini, F.; Villani, C., Atropisomerism inHindered Naphthyl Sulfones Investigated by Dynamic NMR and Dynamic HPLCTechniques, J. Org. Chem., 1995, 60, 5515.

23. Hamper, B.C.; Dukesherer, D.R.; Moedritzer, K., Analytical and PreparativeSeparation of the Enantiomers of Pyrazole Phenyle Ether Herbicides on ThreeChiral Stationary Phases., J. Chrom., 1994, 666, 479-484.

24. Suarez, M.; Schuster, G.B., Photoresolution of an Axially ChiralBicyclo[3.3.0]octan-3-one: Phototriggers for a Liquid-Crystal-Based Optical Switch,J. Amer. Chem. Soc., 1995, 117, 6732.

25. Lalonde, J.J.; Govardhan, C.; Khalaf, N.; Martinez, A.G.; Visuri, K.; Margolin,A.L., Cross-linked Crystals of Candida Rugosa Lipase: Highly Effiecient Catalystfor the Resolution of Chiral Esters, J. Amer. Chem. Soc., 1995, 117, 6845.

26. Welch, C.J.; Perrin, S.R., The Whelk-O 1 Chiral Stationary Phase: Some RecentDevelopments, Poster presented at the 4th International Symposium on ChiralDiscrimination, Sept. 22, 1993, Montréal.

27. Stringham, R.W., Relationship Between Resolution and Analysis Time in ChiralSubcritical Fluid Chromatography, Chirality, 1996, 8, 249-257.

28. Courtesy of Suzanne Leung, Department of Pharmaceutics, University ofMinnesota.

29. Courtesy of Dhimant Desai, American Health Foundation.30. Courtesy of Hal Butler, Sepracor, Inc.31. Courtesy of Allan Rettie, Department of Medicinal Chemistry, University of

Washington.32. Courtesy of Chet Mathis, Department of Radiology, University of Pittsburgh

School of Medicine.33. Welch, C.J.; Perrin. S.R., Improved Chiral Stationary Phase for ß-blocker

Enantioseparations, J. Chromatogr., 1995, 690, 218.34. Pirkle, W.H.; Burke, J.A., Preparation of a Chiral Stationary Phase from an

α-amino Phosphonate, Chirality, 1989, 1, 57.35. Pirkle, W.H.; Burke, J.A., Chiral Stationary Phase Designed for β-blockers,

J. Chromatogr., 1991, 557, 173,.36. Perrin, S.R., “Fast Liquid Chromatography for the Analysis of Enantiomers” In

Pharmaceutical and Biomedical Applications of Liquid Chromatography; Riley,M., Lough, W.J., Wainer, Eds.; Pergamon Division of Elsevier Science Ltd.:Oxford, 1994; Vol. 1, Chapter 3.

37. Courtesy of Les Dolak, Department of Chemical & Biological Screening,Pharmacia & Upjohn, Inc.

38. Pirkle, W.H.; Gan, K.Z.; Brice, L.J., The Enhancement of Enantioselectivity byHalogen Substitutes, Tetrahedron: Asymmetry, 1996, 7, 2813-2816.

39. Pirkle, W.H.; Gan, K.Z., in press, 1997.40. Pirkle, W.H.; Brice, L.J.; Caccamese, S.; Principato, G.; Failla, S.,

J. Chromatogr., 1996, 721, 241-246.41. Pirkle, W.H.; Koscho, M.E.; Wu, Z., High-Performance Liquid Chromatographic

Separation of the Enantiomers of N-Aryloxazolinones, N-aryl Thiazolinones andtheir Sulfur Derivatives on a Synthetic Chiral Stationary Phase, J. Chromatogr.,1996, 726, 91-97.

42. Pirkle, W.H.; Koscho, M.E., J. Chrom, in press, 1997.43. Szczerba & Welch, Regis Technologies, Inc., unpublished results.44. Caccamese, S., Tetrahedron: Asymetry, 1996, 7, 2577-2584.45. Kennedy, J.K., Comparison of Chiral Separations on Polysaccharide Chiral

Stationary Phases to an Improved Pirkle Phase, J. Chromatogr., 1996, 725, 219-224.

46. Szczerba, T. J., Regis Technologies, Inc., unpublished results.47. Uray, G.; Kosjek, B., Simultaneous Enantioseparation of Flobufen and its

Diastereomeric Metabolites on a Pirkle Type Chiral Stationary Phase, Poster presented at the 11th International Symposium on Chiral Discrimination, July 25, 1999, Chicago.

48. Courtesy of Georg Uray, Karl Franzens University, Austria; Norbert Maier,University of Vienna, Austria; Wolfgang Lindner, University of Vienna, Austria.

49. Pirkle, W.H.; Lee, W.; Welch, C.J., Enantiomer, 1997, 2, 423-431.50. Pirkle, W.H.; Lee, W., Bull. Kor. Chem. Soc., 1998, 19(11), 1277-1280.51. Lee, W., Bull. Kor. Chem. Soc., 1998, 19(7), 715-717.52. Hyun, M.H.; Jin, J.S.; Lee, W., Bull. Kor. Chem. Soc., 1997, 18(3), 336-339.53. Kim, S.W.; Ahn, S.Y.; Koh, J.S.; Lee, J.H.; and Cho, H.Y., Tetrahedron Letters,

1997, 38(26), 4603-4606.54. Lee, W.; Kim, B.H, J. Of High Resolution Chromatogr., 1998, 21(3), 189-192.55. Courtesy of Wonjae Lee, LG Chemicals, Korea.56. Lee, J.Y.; Lee, Y.S.; Chung, B.Y.; Park, H., Tetrahedron, 1997, 53(7), 2449-

2458.57. Lee Wonjae, Analytical Lett., 1997, 30(15), 2791-2799.58. K. Gyimesi-Forras, Gy. Szasz, M. Szabo and J. Kokosi: Chiral liquid

chromatographic separation of new potential cholecystokinin antagonist nitrogen-containing heterocycles, Poster presented at the 12th International Symposium onChiral Discrimination, Sept. 24, 2000, Chamonix.

59. Courtesy of Dr. Francesco Gasparrini, Misiti,Villani, et al,; Rome University “La Sapienza.”

60. Courtesy of Georg Uray, Karl Franzens University, Austria.

REFERENCES

NOTESIf you have published literature or intend to publish literature referencing anyof Regis’ columns (Pirkle-types or others), we would appreciate a copy for ourfiles. Please send it directly to Regis (address at right).Regis would appreciate the opportunity of obtaining your permission to reference your material in our Application Guides. Please let us know if youhave application information you would like included in our future guides.PLEASE CONTACT REGIS FOR MORE INFORMATION.

8210 Austin AvenueMorton Grove, IL 60053 USA

tel: 847 967-6000 � 800 323-8144fax: 847 [email protected]

website: www.registech.com86 REGIS TECHNOLOGIES CHIRAL APPLICATION GUIDE VI • WWW.REGISTECH.COM/chiral/


INDEX OF APPLICATION BY COMPOUND

Aryl Propionic Acid Non SteroidalAnti-Inflammatory Drugs (NSAIDS)..................................8-11

α-Trityl-2-naphthalenePropionic Acid.....................10

2-(4-Hydroxy-Phenoxy)Propionic Acid.....................10

3,5-Dimethylanilide-R,S-Ibuprofen ............................10

Carprofen...............................11Cicloprofen............................8,9Etodolac...................................8Fenoprofen ...............................8Flurbiprofen ..............................9Hydratropic Acid.....................11Ibuprofen..................................9Indoprofen..............................10Ketoprofen................................8Ketoprofen as 1-naphthylamide...8Loxoprofen ...............................9Naproxen (normal phase) .....9,10Naproxen (reversed phase) ........9Naproxen (semi prep)................8Naproxen Diisopropyl Amide .....9Naproxen Dimethyl Amide .......10Naproxen Methyl Amide..........10Naproxen Methyl Ester ............10Pirprofen ..................................8Rebamipide ............................10Tiaprofenic Acid........................8

Other Carboxylic Acids ..........11-15α-Methoxyphenyl Acetic Acid ...131,1’-Binaphthyl-2,2’-

Diylhydrogen Phosphate .......121-Cyclohexyl-1-phenylacetic

Acid ...................................141-Cyclopentyl-1-phenylacetic

Acid ...................................142-(2-Chloro-4-methylphenoxy)

Propionic Acid.....................142-(3-Chlorophenoxy)

Propionic Acid.....................142-Phenylcyclopropane

Carboxylate ........................122,3-Dibenzoyl-Tartaric Acid ......154-Chloromandelic Acid ............134-(Trifluoromethyl)-

Mandelic Acid.....................15Calcium Channel Blocker .........12Ditoluoyltartaric Acid ...............14Ketorolac................................13Mandelic Acid ........................12Phenylbutyric Acid...................11Phenylsuccinic Acid .................13Suprofen ................................14Tetrahydropyrimidine

Carboxylic Acid...................11Trolox ....................................12Trolox-methylether ...................14Vanilmandelic Acid .................14

Basic Amine ................................15Trans-11,12-Diamino-

9,10-dihydro-9,10-ethanoanthracene ................15

Basic Nitrogen ............................15Troger’s Base..........................15

Esters, Lactones, Ketones, Anhydrides ............................16-19

1’-Acetoxychavicol Acetate.......191,3,5-Triphenylpent-4-yn-1-one ..182-Methyl-1-Indanone ................162-Methyl-1-Tetralone.................183-Methyl-1-Indanone ................17Buckminsterfullerene-Enone

[2+2] Photoadducts..............19Diperodon ..............................18DPHB.....................................17Ethyl-2-(p-Hydroxyphenoxy)

Propionate ..........................19Methyl Mandelate ...................16Tert-butyl-2(benzamido)

cyclopentyl carbamate..........19

Amides, Imides, Carbamates, etc. ....................20-24

β-Lactam.................................24BOC-Ala ................................20CBZ Nornicotine .....................20CBZ-Phe .................................20CBZ-Val..................................20Cyclopentyl Benzoyl-diamide ....24EEDQ ....................................20

Epoxides .....................................24m-Cl-Styrene Oxide..................24Stilbene Oxide........................24Styrene Oxide.........................24

Alcohols.................................25-31α-Naphthyl Methyl Carbinol .....25β-Naphthyl Methyl Carbinol .....261,1’-Bi-2-Naphthol ...................261,1’-Binaphthol

Monomethylether ................281,1,2,-Triphenyl-1,

2-Ethanediol ........................271,2,3,4-Tetrahydro-1-Naphtol ...251-(4-Benzyloxy) Phenyl Ethanol..301-(4-Hydroxyphenyl) Ethanol .....291-(4-Methoxyphenyl)-

2-butanol ............................291-(4-Methoxyphenyl)-

2-propanol ..........................291-[(4-Phenyl) Phenyl] Ethanol .....301-(m-Chlorophenyl) Ethanol .......311-(m-Methylphenyl) Ethanol .......301-(m-Trifluoromethylphenyl)

Ethanol ...............................301-Naphthyl-2-Butanol ...............26

1-(o-Chlorophenyl) Ethanol........311-(o-Methoxyphenyl) Ethanol .....291-(o-Methylphenyl) Ethanol........301-(p-Bromophenyl) Ethanol ........301-(p-Fluorophenyl) Ethanol ........301-(p-Chlorophenyl) Ethanol .......311-(p-Methylphenyl) Ethanol........291-Phenylpentanol .....................271-Phenyl-2-propanol .................292-Methoxyphenyl Phenyl

Carbinol .............................282-Naphthyl-2-Butanol ...............262-Thiopheneethanol .................293-Thiopheneethanol .................299-Anthryl Trifluoromethyl

Carbinol .............................259-Anthrylethanol ......................26Acenaphthenol........................25Ibuprofenol .............................25Methyl 3-Phenyl-3azido-

2hydroxypropanoate (Erythro-diastereomer) ...........29

Phenyl Cyclohexyl Carbinol ......28Phenyl Ethyl Carbinol...............27Phenylethylene Glycol ..............31Phenyl Isopropyl Carbinol ........28Phenyl Methyl Carbinol ............27Phenyl Phenylethyl Carbinol......28Phenyl Propyl Carbinol.............27Phenyl Tribromomethyl

Carbinol .............................27Propafenone ...........................28Ranolazine .............................31Terfenedine.............................28Tert Butyl Phenyl Carbinol ........25Tetrahydrobenzopyrene-7-ol .....26Trans Phenyl Cyclohexanol

(Analytical vs. Preparative Run) ..................28

Diols, Hydroxyketones, etc. ........32Anisoin ..................................32Benzoin..................................32Hydrobenzoin.........................32Ipsdienol ................................32

Sulfoxides..............................33-35Omeprazole ...........................34Pantoprazole ..........................35Sulfinpyrazone........................34

Phosphorous Compounds .......36-38Cyclophosphamide..................36Phosphine Selenium Oxide .......37Secondary Phosphine

Oxide............................37,38Tertiary Phosphine Oxide ....37,38

Atropisomers .........................39-46Adam’s Acid Diethylamide .......46Amlodipine.............................46

Nimodipine ............................46Sulfone Atropisomer ................41Sulfoxide Atropisomer..............41Vapol.....................................46

Optical Switches, Liquid Crystal Components, etc. .............47

Mesogens...............................47Phototriggers...........................47

Allenes ..................................48-52

Organometallic Compounds ...53-55

Agricultural Compounds .........56-60Bromacil.................................56Chlorflurecol Methyl ................58Chrysanthemic Acid-

Ethyl Ester ...........................57Cis:trans Cypermethrin.............59Crotoxyphos ...........................58Devrinol, Napropamide ...........58Diclofop Methyl.......................58Dinocap .................................60Fenvalerate.............................60Fenoxaprop-ethyl.....................60Fluazifop-butyl.........................60Haloxyfop-ethoxyethyl ..............60Leptophos, Phosvel ..................57Mecoprop ..............................57Mecoprop Methyl ...................56Metalaxyl ...............................57Metolachlor ............................57Omite ....................................57Permethrin ..............................56PPO Inhibitors ...............56,58,59Propiconazole, Tilt...................58Quizalofop-ethyl......................60Resmethrin..............................57Sethoxydim.............................57Silvex Methyl ..........................59Tetramethrin............................56Tetramisole .............................59

Miscellaneous Pharmaceuticals61-73Alfuzosin ................................72Althiazide...............................71Bendroflumethiazide ...........61,67Bupivacaine............................62Chlormezanone.......................72Chlorthalidone ........................68Clenbuterol.............................71Coumachlor............................69Cromakalim............................70Cyclandelate ..........................62Cyclothiazide..........................61Dexmedetomidine....................68Dihydrotetrabenazine ..............72Doxazosin ..............................72Ethotoin..................................71Flobufen .................................68

Index of Application by Compound continued on page 88


Flobufen Metabolites................68Fluridil....................................72Hanessian’s Lignan .................63Idazoxan................................73Ifenprodil................................69Indapamide .......................62,67Isoxsuprine .............................70Isradipine (normal phase).........63Isradipine (reversed phase).......63Ketamine................................69Ketoconazole..........................69Lansoprazole ..........................71Lorazepam .............................71Lorglumide..............................73McN 5652.............................62Mephenytoin...........................61Metolazone ............................71Methadone Hydrochloride........71Modafinil ...............................73Mosapride..............................73Nadifloxacin...........................73Nicardipine ............................63Nirvanol.................................61Ofloxacin ...............................70Oxazepam .............................61p-Chloro-Warfarin ...................62Pantoprazole ..........................35Pazufloxacin ...........................72Prilocaine ...............................70Proglumide .............................64Quinazolone Derivatives .....68,69SC 41930..............................63Sulindac.................................73Sulpiride ................................69Temazepam.......................64,70Tetrabenazine.........................72Thalidomide.......................61,67Tofisopam and it’s

Conformers .........................69Tolperisone.............................62Trans-U-50488H......................72Trichlormethiazide ...................70Troglitazone ...........................64Tropicamide ...........................63U-100057 ..............................63U-94863 (analytical) ...............64U-94863 (preparative) .............63Warfarin (normal phase).....68,70Warfarin (reversed phase)........70Zopiclone ...............................71

Barbiturates ................................74Hexobarbital...........................74

Ureas..........................................741-Naphthylureaphenethylamine.74

Diol Epoxides ..............................74r-7,t-8-Dihydroxy-t-9,10-epoxy-

7,8,9,10-tetrahydrobenzo[a]pyrene ............................73

Natural Products ....................75-76

2-cis-4-trans-Abscisic Acid.........752-trans-4-trans-Abscisic Acid......75Abscisic Acid..........................76Abscisic Acid Methyl Ester........75Calanolide A ..........................75Combretastatin D-1..................75Flavanone ..............................75Luciferin .................................76Taxifolin .................................76Tetrahydropalmatine ................76

ß-Blockers..............................76-78Alprenolol ..............................77Atenolol .................................77Bambuterol .............................76Betaxolol ................................77Bufuralol.................................77Bupranolol..............................77Carazolol ...............................78Metoprolol..............................77Nadolol .................................78Oxprenolol .............................78Pindolol..................................78Practolol .................................78Pronethalol .............................78Propranolol.............................78Timolol Maleate ......................78Tulobuterol HCL.......................77

Amino Acids ..........................79-811-Aminoindan .........................791,2,3,4-Tetrahydro-1-

naphthylamine .....................794-Fluorophenylalanine..............79Arginine.................................79DOPA ....................................81Ethionine ................................81Glutamic Acid.........................81Glutamine ..............................80Histidine.................................81p-Hydroxy-Phenylglycine...........80Kynurenine .............................80Leucine...................................79Lysine.....................................81Methionine .............................79Norleucine .............................79Norvaline ...............................80Phenylalanine .........................80Phenylglycine..........................80Serine ....................................80Tryptophan .............................80Tyrosine .................................79

INDEX OF APPLICATION BY COMPOUND continued from page 87


INDEX OF APPLICATION BY COLUMN TYPE

α-Burke .......................................2Alprenolol..............................77Atenolol.................................77Bambuterol ............................76Betaxolol ...............................77Carazolol ..............................78Clenbuterol ............................71Diperodon .............................18Lansoprazole..........................71Methadone Hydrochloride .......71Metoprolol .............................77Omeprazole ..........................34Pantoprazole..........................35Practolol ................................78Pronethalol.............................78Tulobuterol HCL......................77

ChiroSil® RCA(+) and SCA(-)1-Aminoindan ........................791,2,3,4-Tetrahydro-1-naphthylamine........................794-Fluorophenylalanine .............79Arginine ................................79DOPA ...................................81Ethionine ...............................81Glutamic Acid ........................81Glutamine..............................80Histidine ................................81p-Hydroxy-Phenylglycine ..........80Leucine..................................79Lysine....................................81Methionine.............................79Norleucine.............................79Norvaline ..............................80Phenylalanine.........................80Phenylglycine .........................80Serine ...................................80trans-11,12-Diamino-9,10-

dihydro-9,10-ethanoanthracene................15

Tryptophan ............................80Tyrosine.................................79

DACH-DNBβ-Blockers .........................76,77β-Lactam................................24Chlorthalidone .......................68Fenoxaprop-ethyl ....................60Fluazifop-butyl ........................60Haloxyfop-ethoxyethyl .............60Phosphine Selenium Oxide ......37Quizalofop-ethyl .....................60Secondary Phosphine

Oxide ...........................37,38Sulfoxides ..............................34Sulpiride................................69Tertiary Phosphine Oxide ...37,38

ß-GEM 1r-7,t-8-Dihydroxy-t-9,10-epoxy-

7,8,9,10-tetrahydrobenzo[a]pyrene ...........................74

Tofisopam and it’s Conformers .69

LeucineHexobarbital ..........................74Luciferin.................................76

Phenylglycine1-Naphthylureaphenethylamine 74

Pirkle 1-J3,5-Dimethylanalide-R,S-

Ibuprofen............................10Adam’s Acid Diethylamide ......46Bufuralol ................................77Bupranolol .............................77Cis:trans Cypermethrin ............59Oxprenolol ............................78Pindolol .................................78Propranolol ............................78Timolol Maleate......................78Trans-U-50488H.....................72

ULMOα-Trityl-2-naphthalene

Propionic Acid ....................10α-Naphthyl Methyl Carbinol ....25β-Naphthyl Methyl Carbinol.....261,1’-Bi-2-Naphthol ..................261,1’-Binaphthol

Monomethylether.................281,1,2,-Triphenyl-1,2-

Ethanediol ..........................271,2,3,4-Tetrahydro-1-

Naphtol .............................251,3,5-Triphenylpent-4-yn-1-one 181-Cyclohexyl-1-

phenylacetic Acid................141-Cyclopentyl-1-

phenylacetic Acid................141-(4-Benzyloxy) Phenyl

Ethanol...............................301-(4-Hydroxyphenyl) Ethanol ....291-(4-Methoxyphenyl)-2-butanol..291-(4-Methoxyphenyl)-

2-propanol .........................291-[(4-Phenyl) Phenyl] Ethanol ....301-(m-Chlorophenyl) Ethanol ......311-(m-Methylphenyl) Ethanol ......301-(m-Trifluoromethylphenyl)

Ethanol...............................301-Naphthyl-2-Butanol...............261-(o-Chlorophenyl) Ethanol .......311-(o-Methoxyphenyl) Ethanol ....291-(o-Methylphenyl) Ethanol .......301-(p-Bromophenyl) Ethanol .......30

1-(p-Chlorophenyl) Ethanol.......311-(p-Fluorophenyl) Ethanol........301-(p-Methylphenyl) Ethanol .......301-Phenylpentanol ....................271-Phenyl-2-propanol ................292-(2-Chloro-4-methylphenoxy)

Propionic Acid ....................142-(4-Hydroxy-Phenoxy)

Propionic Acid ....................102-Methoxyphenyl Phenyl

Carbinol.............................282-Naphthyl-2-Butanol...............262-Thiopheneethanol.................292,3-Dibenzoyl-Tartaric Acid .....153-Thiopheneethanol.................299-Anthryl Trifluoromethyl

Carbinol.............................259-Anthrylethanol .....................26Acenaphthenol .......................25Althiazide ..............................71Bendroflumethiazide ...............67Calcium Channel Blocker.........12Cyclothiazide.........................61Cyclopentyl Benzoyl-diamide ...24Ditoluoyltartaric Acid ..............14Etodolac ..................................8Flobufen Metabolites ...............68Flobufen ................................68Indapamide ...........................67Ketoprofen as 1-

naphthylamide ......................8Methyl 3-Phenyl-3azido-

2-hydroxypropanoate (Erythro-diastereomer) ..........29

Naproxen................................9Phenyl Cyclohexyl Carbinol .....28Phenyl Ethyl Carbinol ..............27Phenyl Isopropyl Carbinol........28Phenyl Methyl Carbinol ...........27Phenyl Phenylethyl Carbinol .....28Phenyl Propyl Carbinol ............27Phenyl Tribromomethyl

Carbinol.............................27Phenylbutyric Acid ..................11Phenylsuccinic Acid ................13Prilocaine ..............................70Temazepam ...........................64Tert Butyl Phenyl Carbinol........25Tetrahydropyrimidine

Carboxylic Acid ..................11Thalidomide ...........................67Trans Phenyl Cyclohexanol

(Analytical vs. Preparative Run)..................28

Trichlormethiazide ..................70Trolox....................................12Trolox-methylether ...................14Vapol ....................................46Warfarin ...............................68

Whelk-O 1 and 2α-Methoxyphenyl Acetic Acid......................................131’-Acetoxychavicol Acetate ......191,1’-Binaphthyl-2,2’-

Diylhydrogen Phosphate.......122-(3-Chlorophenoxy)

Propionic Acid ....................142-cis-4-trans-Abscisic Acid .......752-Methyl-1-Indanone................162-Methyl-1-Tetralone................182-Phenylcyclopropane

Carboxylate........................122-trans-4-trans-Abscisic Acid.....753-Methyl-1-Indanone................174-Chloromandelic Acid............134-(Trifluoromethyl)-

Mandelic Acid ....................15Abscisic Acid .........................76Abscisic Acid Methyl Ester .......75Alfuzosin ...............................72Amlodipine ............................46Anisoin..................................32Bendroflumethiazide ...............61Benzoin .................................32BOC-Ala................................20Bromacil ................................56Buckminsterfullerene-Enone

[2+2] Photoadducts .............19Bupivacaine ...........................62Calanolide A .........................75Carprofen..............................11CBZ nornicotine .....................20CBZ-Phe ................................20CBZ-Val .................................20Chlorflurecol Methyl ................58Chlormezanone......................72Chrysanthemic Acid-

Ethyl Ester...........................57Cicloprofen...........................8,9Combretastatin D-1 .................75Coumachlor ...........................69Cromakalim ...........................70Crotoxyphos ..........................58Cyclandelate..........................62Cyclophosphamide .................37Devrinol, Napropamide...........58Dexmedetomidine ...................68Diclofop Methyl ......................58Dihydrotetrabenazine..............72Dinocap ................................60Doxazosin .............................72DPHB ....................................17EEDQ....................................20Ethotoin .................................71Ethyl-2-(p-Hydroxyphenoxy)

Propionate..........................19Fenvalerate ............................60Fenoprofen ..............................8

Index of Application by Column Type continued on page 90


INDEX OF APPLICATION BY COLUMN TYPE continued from page 89

Flavanone..............................75Flurbiprofen .............................9Fluridil ...................................72Hanessian’s Lignan .................63Hydrobenzoin ........................32Hydratropic Acid....................11Ibuprofen.................................9Ibuprofenol ............................25Idazoxan ...............................73Ifenprodil ...............................69Indapamide ...........................62Indoprofen .............................10Ipsdienol................................32Isoxsuprine.............................70Isradipine (normal phase) ........63Isradipine (reversed phase) ......63Ketamine ...............................69Ketoconazole .........................69Ketoprofen...............................8Ketorolac ...............................13Kynurenine.............................80Leptophos, Phosvel..................57Lorazepam.............................71Lorglumide .............................73Loxoprofen...............................9Mandelic Acid .......................12m-Cl-Styrene Oxide .................24McN 5652 ............................62Mecoprop..............................57Mecoprop Methyl ...................56Mephenytoin..........................61Mesogens ..............................47Metalaxyl ..............................57Methyl Mandelate...................16Metolachlor............................57Metolazone............................71Modafinil...............................73Mosapride .............................73Nadifloxacin..........................73Nadolol.................................78Naproxen (normal phase).....9,10Naproxen (reversed phase) .......9Naproxen (semi prep) ...............8Naproxen Diisopropyl Amide ....9Naproxen Dimethyl Amide ......10Naproxen Methyl Amide .........10Naproxen Methyl Ester............10Nicardipine ...........................63Nimodipine............................46Nirvanol ................................61Ofloxacin ..............................70Omite....................................57Oxazepam ............................61p-Chloro-Warfarin...................62Pazufloxacin ..........................72Permethrin .............................56Phenylethylene Glycol .............31Phototriggers ..........................47Pirprofen..................................8PPO Inhibitors ..............56,58,59Proglumide ............................64Propafenone ..........................28

Propiconazole, Tilt ..................58Quinazolone Derivatives ....68,69Ranolazine.............................31Rebamipide ...........................10Resmethrin .............................57SC 41930 .............................63Sethoxydim ............................57Silvex Methyl .........................59Stilbene Oxide .......................24Styrene Oxide ........................24Sulfinpyrazone .......................34Sulfone Atropisomer................41Sulfoxide Atropisomer .............41Sulindac ................................73Suprofen................................14Taxifolin ................................76Temazepam ...........................70Terfenadine............................28Tert-butyl-2(benzamido)

cyclopentyl carbamate ........19Tetrabenazine ........................72Tetrahydrobenzopyrene-7-ol.....26Tetrahydropalmatine ...............76Tetramethrin ...........................56Tetramisole ............................59Thalidomide ...........................61Tiaprofenic Acid.......................8Tolperisone ............................62Troger’s Base .........................15Troglitazone...........................64Trolox....................................12Tropicamide...........................63U-100057 .............................63U-94863 ..........................63,63Vanilmandelic Acid.................14Warfarin (normal phase) .........70Warfarin (reversed phase) .......70Zopiclone ..............................71

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Compound Structure/Name

This compound � may or � may notbe used in an application booklet.

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�

Stability/Exposure:Light � Stable � Decomposes � Unknown

Moisture � Stable � Decomposes � Unknown

Temp<40˚C � Stable � Decomposes � Unknown

ACIDS:

Acetic Acid (<1%) � Stable � Decomposes � Unknown

Trifluoroacetic Acid (<1%) � Stable � Decomposes � Unknown

BASES:

Triethylamine (<1%) � Stable � Decomposes � Unknown

Diethylamine (<1%) � Stable � Decomposes � Unknown

Storage Conditions:____________________________________________________________________________________________

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SolubilityWater � Soluble � Slightly � Decomposes � Unknown

Methanol � Soluble � Slightly � Decomposes � Unknown

Ethanol � Soluble � Slightly � Decomposes � Unknown

2-Propanol � Soluble � Slightly � Decomposes � Unknown

Hexane � Soluble � Slightly � Decomposes � Unknown

Ethyl Acetate � Soluble � Slightly � Decomposes � Unknown

CH2Cl2 � Soluble � Slightly � Decomposes � Unknown

Acetonitrile � Soluble � Slightly � Decomposes � Unknown

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Chromatographic Analysis:

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Chiral Screening Data Sheet

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chiral application guide - hplc · column, compares favorably with polysaccharide-derived chiral...

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