graphical abstract: adv. synth. catal. 18/2010

succeeding Journal f�r praktischeChemie

(founded in 1828)

2010, 352, 18, Pages 3101 – 3452

Issue 17/2010 was published online onNovember 19, 2010

AIMS AND SCOPEAlthough total synthesis reached extraordinary levels of sophistication in the lastcentury, the development of practical and efficient synthetic methodologies is stillin its infancy. Achieving chemical reactions that are highly selective, economical,safe, resource- and energy-efficient, and environmentally benign is a primarychallenge to chemistry in this century. Realizing this goal will demand the highestlevel of scientific creativity, insight and understanding in a combined effort byacademic, government and industrial chemists and engineers.Advanced Synthesis & Catalysis promotes that process by publishing high-impactresearch results reporting the development and application of efficient syntheticmethodologies and strategies for organic targets that range from pharmaceuticalsto organic materials. Homogeneous catalysis, biocatalysis, organocatalysis andheterogeneous catalysis directed towards organic synthesis are playing an everincreasing role in achieving synthetic efficiency. Asymmetric catalysis remains atopic of central importance. In addition, Advanced Synthesis & Catalysis includesother areas that are making a contribution to green synthesis, such as synthesisdesign, reaction techniques, flow chemistry and continuous processing, multi-phase catalysis, green solvents, catalyst immobilization and recycling, separationscience and process development.Practical processes involve development of effective integrated strategies, froman elegant synthetic route based on mechanistic and structural insights at themolecular level through to process optimization at larger scales. These endeavorsoften entail a multidisciplinary approach that spans the broad fields chemistry,biology, and engineering and involve contributions from academic, government,and industrial laboratories.The unique focus of Advanced Synthesis & Catalysis has rapidly made it theleading organic chemistry and catalysis journal. The goal of Advanced Synthesis& Catalysis is to help inspire a new era of chemical science, based on the efforts ofsynthetic chemists and on interdisciplinary collaboration, so that chemistry willmake an even greater contribution to the quality of life than it does now.

COMMENTARY

Commentary on “A New, Efficient and Recyclable LanthanumACHTUNGTRENNUNG(III) Oxide-Catalyzed C–NCross-Coupling” by S. Narayana Murthy, B. Madhav, V. Prakash Reddy, and Y. V. D.Nageswar, Adv. Synth. Catal. 2010, 352, 3241–3245

Adv. Synth. Catal. 2010, 352, 3119 – 3120

Brett P. Fors, Stephen L. Buchwald

3119

COMMUNICATIONS

Iridium-Catalyzed Enantioselective Hydrogenation of CyclicImines

Adv. Synth. Catal. 2010, 352, 3121 – 3125

Mingxin Chang,* Wei Li, Guohua Hou, Xumu Zhang*

3121

Adv. Synth. Catal. 2010, 352, 3103 – 3112 � 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 3103

Novel Amido-Complexes for the Efficient AsymmetricHydrogenation of Imines

Adv. Synth. Catal. 2010, 352, 3126 – 3130

Kathrin Kutlescha, Torsten Irrgang, Rhett Kempe*

3126

Synergistic Effect: Hydroalkoxylation of Allenes throughCombination of Enantiopure BIPHEP-Gold Complexes andChiral Anions

Adv. Synth. Catal. 2010, 352, 3131 – 3135

Kohsuke Aikawa, Masafumi Kojima, Koichi Mikami*

3131

Highly Diastereoselective Indium-Mediated Allenylation ofN-tert-Butanesulfinyl Imino Ester: Efficient Synthesis ofOptically Active a-Allenylglycines

Adv. Synth. Catal. 2010, 352, 3136 – 3140

Shen-Shuang Jin, Ming-Hua Xu*

3136

Ruthenium-Catalyzed Cascade N- and C(3)-Dialkylation ofCyclic Amines with Alcohols Involving HydrogenAutotransfer Processes

Adv. Synth. Catal. 2010, 352, 3141 – 3146

Basker Sundararaju, Zhou Tang, Mathieu Achard,Gangavaram V. M. Sharma, Lo�c Toupet, Christian Bruneau*

3141

Organocatalytic Enantioselective Strecker Synthesis ofa-Quaternary a-Trifluoromethyl Amino Acids

Adv. Synth. Catal. 2010, 352, 3147 – 3152

Dieter Enders,* Katharina Gottfried, Gerhard Raabe

3147

Table of Contents

3104 asc.wiley-vch.de � 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Adv. Synth. Catal. 2010, 352, 3103 – 3112

http://asc.wiley-vch.de

Iridium-Catalyzed Asymmetric Allylic Amination with PolarAmines: Access to Building Blocks with Lead-LikeMolecular Properties

Adv. Synth. Catal. 2010, 352, 3153 – 3157

Paolo Tosatti, Joachim Horn, Amanda J. Campbell,David House, Adam Nelson,* Stephen P. Marsden*

3153

Ligand-Free Copper-Catalyzed Amination of HeteroarylHalides with Alkyl- and Arylamines

Adv. Synth. Catal. 2010, 352, 3158 – 3162

Zhen-Jiang Liu, Jean-Pierre Vors, Ernst R. F. Gesing,*Carsten Bolm*

3158

Development of a Mild Procedure for the Addition ofBisulfite to Electrophilic Olefins

Adv. Synth. Catal. 2010, 352, 3163 – 3168

Francesco Fini, Murali Nagabelli, Mauro F. A. Adamo*

3163

Ruthenium Pincer-Catalyzed Acylation of Alcohols UsingEsters with Liberation of Hydrogen under NeutralConditions

Adv. Synth. Catal. 2010, 352, 3169 – 3173

Boopathy Gnanaprakasam, Yehoshoa Ben-David,David Milstein*

3169

Highly Enantioselective Zinc-Catalyzed Friedel–CraftsAlkylation of Indoles with Ethyl Trifluoropyruvate

Adv. Synth. Catal. 2010, 352, 3174 – 3178

Yonghai Hui, Weiliang Chen, Wentao Wang, Jun Jiang,Yunfei Cai, Lili Lin, Xiaohua Liu,* Xiaoming Feng*

3174

Adv. Synth. Catal. 2010, 352, 3103 – 3112 � 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim asc.wiley-vch.de 3105


Lewis Acid-Catalyzed Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates: A New Efficient Route to2-Styrylmalonates

Adv. Synth. Catal. 2010, 352, 3179 – 3184

Alexey O. Chagarovskiy, Olga A. Ivanova,Eduard R. Rakhmankulov, Ekaterina M. Budynina,Igor V. Trushkov, Mikhail Ya. Melnikov*

3179

Excess Phosphine Ligand Plays a Critical Role in theAsymmetric Copper(I) Iodide-Catalyzed ConjugateAddition of Grignard Reagents to a,b-Unsaturated Esters

Adv. Synth. Catal. 2010, 352, 3185 – 3189

Shun-Yi Wang, Ping Song, Teck-Peng Loh*

3185

A Mild Catalytic Oxidation System: Ruthenium Porphyrinand 2,6-Dichloropyridine N-Oxide Applied for AlkeneDihydroxylation

Adv. Synth. Catal. 2010, 352, 3190 – 3194

Wen-Xiang Hu,* Pei-Rong Li, Gaoxi Jiang, Chi-Ming Che,*Jian Chen*

3190

Lewis Acid-Catalyzed C–H Functionalization for Synthesisof Isoindolinones and Isoindolines

Adv. Synth. Catal. 2010, 352, 3195 – 3200

Bo Qian, Shengmei Guo, Chungu Xia, Hanmin Huang*

3195

Organocatalytic Enantioselective Aziridination of a-Substituted a,b-Unsaturated Aldehydes: AsymmetricSynthesis of Terminal Aziridines

Adv. Synth. Catal. 2010, 352, 3201 – 3207

Luca Deiana, Gui-Ling Zhao,* Shuangzheng Lin,Pawel Dziedzic, Qiong Zhang, Hans Leijonmarck,Armando C�rdova*

3201

Table of Contents



Multicomponent Synthesis of 1,2,3-Triazoles in WaterCatalyzed by Copper Nanoparticles on Activated Carbon

Adv. Synth. Catal. 2010, 352, 3208 – 3214

Francisco Alonso,* Yanina Moglie, Gabriel Radivoy,Miguel Yus*

3208

Chemoselective Cascade Synthesis of N-Fused Heterocyclesvia Silver(I) Triflate-Catalyzed Friedel–Crafts/N-C BondFormation Sequence

Adv. Synth. Catal. 2010, 352, 3215 – 3222

Lu Hao, Yingming Pan, Tao Wang, Min Lin, Li Chen,Zhuang-ping Zhan*

3215

Aerobic Oxidative Coupling of o-Xylene: Discovery of2-Fluoropyridine as a Ligand to Support SelectivePd-Catalyzed C–H Functionalization

Adv. Synth. Catal. 2010, 352, 3223 – 3229

Yusuke Izawa, Shannon S. Stahl*

3223

Selective C3–C3 Oxidative Cross-Coupling betweenUnactivated Anilines and Indoles

Adv. Synth. Catal. 2010, 352, 3230 – 3234

Linfei Wang, Zhaomeng Han, Renhua Fan*

3230

Synthesis of Dienes by Palladium-Catalyzed Couplings ofTosylhydrazones with Aryl and Alkenyl Halides

Adv. Synth. Catal. 2010, 352, 3235 – 3240

Jos� Barluenga,* Mar�a Tom�s-Gamasa, Fernando Aznar,Carlos Vald�s*

3235

A New, Efficient and Recyclable LanthanumACHTUNGTRENNUNG(III) Oxide-Catalyzed C–N Cross-Coupling

Adv. Synth. Catal. 2010, 352, 3241 – 3245

S. Narayana Murthy, B. Madhav, V. Prakash Reddy,Y. V. D. Nageswar*

3241



FULL PAPERS

Highly Active and Enantioselective Rhodium-CatalyzedAsymmetric 1,4-Addition of Arylboronic Acid to a,b-Unsaturated Ketone by using Electron-Poor MeO-F12-BIPHEP

Adv. Synth. Catal. 2010, 352, 3247 – 3254

Toshinobu Korenaga,* Ryota Maenishi, Keigo Hayashi,Takashi Sakai*

3247

Synthesis of Amido-N-imidazolium Salts and theirApplications as Ligands in Suzuki–Miyaura Reactions:Coupling of Heteroaromatic Halides and the Synthesis ofMilrinone and Irbesartan

Adv. Synth. Catal. 2010, 352, 3255 – 3266

Manian Rajesh Kumar, Kyungho Park, Sunwoo Lee*

3255

Synthesis of Methylene-Bridge Polyarenes throughPalladium-Catalyzed Activation of Benzylic Carbon-Hydrogen Bond

Adv. Synth. Catal. 2010, 352, 3267 – 3274

Chien-Chi Hsiao, Yi-Kuan Lin, Chia-Ju Liu, Tsun-Cheng Wu,Yao-Ting Wu*

3267

An Economical, Green Pathway to Biaryls: PalladiumNanoparticles Catalyzed Ullmann Reaction in Ionic Liquid/Supercritical Carbon Dioxide System

Adv. Synth. Catal. 2010, 352, 3275 – 3286

Jinsheng Cheng,* Longhua Tang, Jingying Xu*

3275

Table of Contents



Study on the Reactivity of Aldehydes in Electrolyzed IonicLiquids: Benzoin Condensation – Volatile OrganicCompounds (VOCs) vs. Room Temperature Ionic Liquids(RTILs)

Adv. Synth. Catal. 2010, 352, 3287 – 3292

I. Chiarotto,* M. Feroci, M. Orsini, M. M. M. Feeney,A. Inesi*

3287

Inter- and Intramolecular Hydroamination of UnactivatedAlkenes Catalysed by a Combination of Copper and SilverSalts: The Unveiling of a Brønstedt Acid Catalysis

Adv. Synth. Catal. 2010, 352, 3293 – 3305

Christophe Michon,* Florian Medina, Fr�d�ric Capet,Pascal Roussel, Francine Agbossou-Niedercorn*

3293

Non-Magnetic and Magnetic Supported Copper(I) ChelatingAdsorbents as Efficient Heterogeneous Catalysts and CopperScavengers for Click Chemistry

Adv. Synth. Catal. 2010, 352, 3306 – 3320

Alicia Megia-Fernandez, Mariano Ortega-MuÇoz,Javier Lopez-Jaramillo, Fernando Hernandez-Mateo,Francisco Santoyo-Gonzalez*

3306

Readily Accessible Oxazolidine Nitroxyl Radicals:Bifunctional Cocatalysts for Simplified Copper BasedAerobic Oxidation

Adv. Synth. Catal. 2010, 352, 3321 – 3328

Christopher J. Gartshore, David W. Lupton*

3321

Chiral Amino Diol Derivatives as New ModularOrganocatalysts for the Enantioselective a-Chlorination ofCyclic b-Keto Esters

Adv. Synth. Catal. 2010, 352, 3329 – 3338

Pablo Etayo, Ram�n Badorrey, Mar�a D. D�az-de-Villegas,*Jos� A. G�lvez*

3329



(Cyclopentadienyl)ruthenium-Catalyzed Regio- andEnantioselective Decarboxylative Allylic Etherification ofAllyl Aryl and Alkyl Carbonates

Adv. Synth. Catal. 2010, 352, 3339 – 3347

Martina Austeri, David Linder, J�r�me Lacour*

3339

Trimethylchlorosilane and Silicon Tetrachloride in TwoNovel Methodologies for the Efficient and Mild AldolAddition of b-Keto Esters and Malonates to Aldehydes

Adv. Synth. Catal. 2010, 352, 3348 – 3354

Antonio Massa,* Ada Roscigno, Paolo De Caprariis,Rosanna Filosa, Antonia Di Mola

3348

Multicomponent Cascade Reactions: A Novel and ExpedientApproach to Functionalized Indoles by an UnprecedentedNucleophilic Addition-Heterocyclization-OxidativeAlkoxycarbonylation Sequence

Adv. Synth. Catal. 2010, 352, 3355 – 3363

Bartolo Gabriele,* Lucia Veltri, Giuseppe Salerno,Raffaella Mancuso, Mirco Costa

3355

Stereocontrolled Construction of Quaternary Stereocentersby Inter- and Intramolecular Nitro-Michael AdditionsCatalyzed by Bifunctional Thioureas

Adv. Synth. Catal. 2010, 352, 3364 – 3372

Rub�n Manzano, Jos� M. Andr�s, Mar�a D. Muruz�bal,Rafael Pedrosa*

3364

Brønsted Base-Catalyzed Tandem Isomerization–MichaelReactions of Alkynes: Synthesis of Oxacycles and Azacycles

Adv. Synth. Catal. 2010, 352, 3373 – 3379

Hongjun Liu, Wei Feng, Choon Wee Kee, Dasheng Leow,Wei-Tian Loh, Choon-Hong Tan*

3373

Table of Contents



Regio- and Stereoselective Biohydroxylations with aRecombinant Escherichia coli Expressing P450pyr

Monooxygenase of Sphingomonas Sp. HXN-200

Adv. Synth. Catal. 2010, 352, 3380 – 3390

Wei Zhang, Weng Lin Tang, Zunsheng Wang, Zhi Li*

3380

One-Pot Conversion of l-Threonine into l-Homoalanine:Biocatalytic Production of an Unnatural Amino Acid from aNatural One

Adv. Synth. Catal. 2010, 352, 3391 – 3398

Eulsoo Park, Minji Kim, Jong-Shik Shin*

3391

Catalytic Asymmetric Inverse-Electron-Demand (IED)[4+2] Cycloaddition of Salicylaldimines: Preparation ofOptically Active 4-Aminobenzopyran Derivatives

Adv. Synth. Catal. 2010, 352, 3399 – 3406

Luca Bernardi, Mauro Comes-Franchini,Mariafrancesca Fochi,* Virginia Leo, Andrea Mazzanti,Alfredo Ricci

3399

Stereoselective Tandem Epoxidation–Alcoholysis/Hydrolysisof Glycals with Molybdenum Catalysts

Adv. Synth. Catal. 2010, 352, 3407 – 3418

Irene Mar�n, M. Isabel Matheu, Yolanda D�az,*Sergio Castill�n*

3407



Retro-Diels–Alder Reactions of Masked CyclopentadienonesCatalyzed by Heterogeneous Brønsted Acids

Adv. Synth. Catal. 2010, 352, 3419 – 3430

Anneleen L. W. Demuynck, Pieter Levecque, Aklilu Kidane,David W. Gammon,* Eugene Sickle, Pierre A. Jacobs,Dirk E. De Vos, Bert F. Sels*

3419

UPDATES

Copper-Catalyzed Cascade Reactions of Substituted4-Iodopyrazolecarbaldehydes with 1,2-Phenylenediaminesand 2-Aminophenols

Adv. Synth. Catal. 2010, 352, 3431 – 3437

Maloy Nayak, Sanjay Batra*

3431

Pyridine-Directed Organolithium Addition to an Enol Ether

Adv. Synth. Catal. 2010, 352, 3438 – 3442

Jingyue Yang, Gregory B. Dudley*

3438

Improved Synthesis of 1,2-Bis(trimethylsilyl)benzenes usingRieke-Magnesium or the Entrainment Method

Adv. Synth. Catal. 2010, 352, 3443 – 3449

Andreas Lorbach, Christian Reus, Michael Bolte,Hans-Wolfram Lerner, Matthias Wagner*

3443

CORRIGENDA

In the communication by Saumen Hajra, Biswajit Maji and Dipakranjan Mal, in Issue 6, 2009, pp 859–864 (DOI: 10.1002/adsc.200800603), on p. 862 the optical rotation ([a]D

25) of compound 6 should read +19.9 (c 1.0, CHCl3) instead of �19.9(c 1.3, CHCl3). Hence the absolute configurations of 2, 36, 6, 7 and 8 should correspond to those of the enantiomers. Theauthors apologize for this error. The corresponding corrections have been made in the Supporting Information.

In the communication by Yu Yuan, Isabelle Thom�, Seok Hwan Kim, Duanteng Chen, Astrid Beyer, Julien Bonnamour, ErikZuidema, Sukbok Chang, and Carsten Bolm in Issue 17, 2010, pp. 2892 – 2898 (DOI: 10.1002/adsc.201000575), in Table 1 onpage 2893, the isomeric ratios for entries 8 and 9 should each read m:o = 52:48. The editorial office apologizes for this error.

Supporting information on the WWW (see article for access details). *Author to whom correspondence should be addressed.

Table of Contents



graphical abstract: adv. synth. catal. 18/2010

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