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Imprimatur:
Date, Signaturetc2120ss.fm 10/14/20
Reviews and Full Papers in Chemical Synthesis
2020Vol. 52, No. 21
November ISynthesis
Synthesis
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Synthesis 2020, 52, 3095–3110DOI: 10.1055/s-0040-1707149
R. Loska*M. Mąkosza*Polish Academy of Sciences, Poland
Synthesis
as
Introduction of Carbon Substituents into Nitroarenes via Nucleophilic Substitution of Hydrogen: New Developments
R1
NO2
X
R2
R1
NOO
R2R3
R3X
H
R1
R2
R3H
NO2
R1
R2
R3X
NO2
1) – HX2) H
[O]
VNS
ONSH
H
H
(+ para isomer)
σH adduct
Review
3095
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Synthesis 2020, 52, 3111–3128DOI: 10.1055/s-0040-1707225
J. B. Mateus-RuizA. Cordero-Vargas*Universidad Nacional Autónoma de México, México
Visible-Light-Mediated Photoredox Reactions in the Total Synthesis of Natural Products
N
O
N
O
H
H
HH
NH
N
HCbz
N
NHMe
O
HO
O O
NH
NO
CO2Me
Photoredox catalysis
e-
hν
SETH
H
O
H
HOO
OH
H
N N
OH
H
CO2Et
e-e-
e-
OHO
Me
OH
OH
Me
O
O
O
O
OH
OH
OH
Et
OH
Et
OH
S
hort Review3111
Imprimaturhttps://doi.org/10.1055/s-0040-1707225https://doi.org/10.1055/s-0040-1707149
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VI
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Synthesis 2020, 52, 3129–3139DOI: 10.1055/s-0040-1707247
C. Moberg*KTH Royal Institute of Technolo-gy, Sweden
Synthesis
Synthesis
is s
t
Silylboranes as Powerful Tools in Organic Synthesis: Stereo- and Regioselective Reactions with 1,n-Enynes
S
hort Review3129
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Synthesis 2020, 52, 3140–3152DOI: 10.1055/s-0040-1707222
M. RehanJ. FlegelF. HeitkampJ. L. PergometF. OtteC. StrohmannK. Kumar*Max-Planck-Institute für Moleku-lare Physiologie, Germany
as
Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators
NO
Ar2
N
Ar1
R
TBSO
NO
NH
Ar1
RO
Ar2
R1
R1
10 mol% Mg(NTf2)2
DCM, 0 °C to rt, 6 h
11 mol% of 3a
NO
NO
ON H
ONH
iPriPr
iPriPr
from E-isomer
yield up to 94%ee up to 99%
33 examples
from Z-isomer
NO
NH
Ar1
RO
Ar2
R1
potent modulators of Hedgehog pathway
Feature
3140
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Synthesis 2020, 52, 3153–3161DOI: 10.1055/s-0040-1707175
L. KadariT. RoisnelW. Erb*P. R. Krishna*F. MonginUniv Rennes, FranceCSIR-Indian Institute of Chemical Technology, India
Remote Deprotometalation-Iodolysis of N,N-Diisopropyl-2-trimethyl-silylferrocenecarboxamide: A New Route Toward 1,1′-Disubstituted Ferrocenes
FeCONiPr2
TMS 1) sBuLi2) I2
FeCONiPr2
I3) tBuOK
80%
FeR
I
15 derivatives10 g in a single batch
Remote functionalization towards 1,1'-disubstituted ferrocenes
PSP
3153
https://doi.org/10.1055/s-0040-1707175https://doi.org/10.1055/s-0040-1707222https://doi.org/10.1055/s-0040-1707247
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VII
Synthesis
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pro
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ted.
Synthesis 2020, 52, 3162–3188DOI: 10.1055/s-0040-1707357
M. Shiri*N. Farajinia-LehiP. SalehiZ. TanbakouchianAlzahra University, IranPakshoo Industrial Group, Second, Iran
Synthesis
Synthesis
is s
t
Transition Metal and Inner Transition Metal Catalyzed Amide Derivatives Formation through Isocyanide Chemistry
S
pecial Topic3162
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Synthesis 2020, 52, 3189–3210DOI: 10.1055/s-0040-1706296
S. R. ManneB. G. de la TorreA. El-Faham*F. Albericio*University of KwaZulu-Natal, South AfricaKing Saud University, Saudi ArabiaAlexandria University, EgyptInstitute for Advanced Chemis-try of Catalonia (IQAC-CSIC), SpainUniversity of Barcelona, Spain
as
OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis
Oxyma-BasedCoupling Reagents
Amides
Esters
Hydroxamic acids
Ureas
Fmoc-protection
Alcohols
Nitriles
Peptides
S
pecial Topic3189
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Synthesis 2020, 52, 3211–3218DOI: 10.1055/s-0040-1707124
B. ZhaoY. Liu*Jiangxi Normal University, P. R. of China
Step-Economical C–H Activation Reactions Directed by In Situ Amidation
LG
O
H
H2N
LG'
in situ
NH
O
H H
HNH
O
H
NH
O
H
C–H activationamidation
enhanced step economy and higher product diversity
S
pecial Topic3211
https://doi.org/10.1055/s-0040-1707124https://doi.org/10.1055/s-0040-1706296https://doi.org/10.1055/s-0040-1707357
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VIII
Synthesis
rictly
pro
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ted.
Synthesis 2020, 52, 3219–3230DOI: 10.1055/s-0040-1707394
N. SpiliopoulouC. T. ConstantinouI. Triandafillidi*C. G. Kokotos*National and Kapodistrian Uni-versity of Athens, Greece
Synthesis
Synthesis
is s
t
Synthetic Approaches to Acyl Hydrazides and Their Use as Synthons in Organic Synthesis
N
OHN
O O
O
O
H
O
NN
O
O
O
X:
- Ar- SR1
- OR2
- NR3R4
- NHOH- NHCOOR5
Easy Synthesis
Acyl Hydrazides
Ease in Scale-up
Useful Synthons
O
O
X
S
pecial Topic3219
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Synthesis 2020, 52, 3231–3242DOI: 10.1055/s-0040-1707133
M. Kolympadi MarkovićD. MarkovićS. Laclef*Université de PicardieJules Verne, France
as
Amide Synthesis by Transamidation of Primary Carboxamides S
pecial Topic3231
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Synthesis 2020, 52, 3243–3252DOI: 10.1055/s-0040-1707132
M. Shiri*Z. Gholami-KoupaeiF. Bandehali-NaeiniM.-S. TonekaboniS. Soheil-MoghaddamD. EbrahimiS. KaramiB. NotashAlzahra University, Iran
Highly Selective Synthesis of -Hydroxy, -Oxy, and -Oxo Amides by a Post-Passerini Condensation Transformation
R'
OHHN
O
R
AcOH
RN
C
R'C
HO
Passeriniadduct
NO
ONHR
OAr
N N
O
O
R
R"
R"
11 examplesyield: 78–88%
14 examplesyield: 68–87%
11 examplesyield: 73–90%
K2CO3MeOH
K2CO3MeOH
1. K2CO3, MeOH2. I2, K2CO3, DMF
N
R"OAc
NHR
OOAr
N
R"OAc
NHR
O
Ph
R'
OAcHN
O
R
S
pecial Topic3243
https://doi.org/10.1055/s-0040-1707132https://doi.org/10.1055/s-0040-1707133https://doi.org/10.1055/s-0040-1707394
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IX
Synthesis
rictly
pro
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ted.
Synthesis 2020, 52, 3253–3262DOI: 10.1055/s-0040-1707174
F. S. MovahedD. N. SawantD. B. BagalS. Saito*Nagoya University, Japan
Synthesis
Synthesis
is s
t
Tris(o-phenylenedioxy)cyclotriphosphazene as a Promoter for the Formation of Amide Bonds Between Aromatic Acids and Amines
S
pecial Topic3253
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Synthesis 2020, 52, 3263–3271DOI: 10.1055/s-0040-1707864
A. V. Smolobochkin*A. S. Gazizov*N. K. OtegenJ. K. VoroninaA. G. StrelnikA. I. SamigullinaA. R. BurilovM. A. PudovikArbuzov Institute of Organic and Physical Chemistry, Russian Federation
as
Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones
NOEt
OEt
O
HNR
R
N
NO Het
n
Het H R
R
H+
PhMe or CHCl3 reflux, 24–64 h
12 examples up to 91% yield
S
pecial Topic3263
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Synthesis 2020, 52, 3272–3276DOI: 10.1055/s-0040-1707809
S. VermaP. KumarA. K. KhatanaD. ChandraA. K. YadavB. TiwariJ. L. Jat*Babasaheb Bhimrao Ambedkar University (A Central University), India
Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media
R1
O
R2 H2O, r.t. to 80 °C
ZnCl2 (10 mol%)
R2
O
NH
R1O
S
OO
HONH2
R1, R2 = aromatic or aliphatic 19 examplesup to 96% yield
Water as solvent
Good to excellent yields
Water-soluble byproduct, hence chromatography-free
Inexpensive catalyst Open to air
Single-step, operationally simple process
+
S
pecial Topic3272
https://doi.org/10.1055/s-0040-1707809https://doi.org/10.1055/s-0040-1707864https://doi.org/10.1055/s-0040-1707174
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X
Synthesis
rictly
pro
hibi
ted.
Synthesis 2020, 52, 3277–3285DOI: 10.1055/s-0040-1707146
C. Q. KabesJ. H. GunnM. A. SelbstR. F. LucasJ. A. Gladysz*Texas A&M University, USA
Synthesis
Synthesis
is s
t
Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H2NCH2CH[(CH2)nNHMe]NH2 (n = 1–4) from -Amino Acids: New Agents for Asymmetric Catalysis
S
pecial Topic3277
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Synthesis 2020, 52, 3286–3294DOI: 10.1055/s-0040-1705892
R. ZhangJ.-C. ZhangW.-Y. ZhangY.-Q. HeH. Cheng*C. Chen*Y.-C. GuHubei University of Arts and Sci-ence, P. R. of ChinaWuhan University of Technolo-gy, P. R. of China
as
A Practical Approach for the Transamidation of N,N-Dimethyl Amides with Primary Amines Promoted by Sodium tert-Butoxide under Solvent-Free Conditions
N R2
O
R1HN R2
O
NaOtBu, rt
Gram-scale reactions with an easy work-up procedure
45–90% yield23 examples
R1 = aliphatic, (hetero)aryl; R2 = H or alkyl
Compatible with long-chain alkyl groups and heteroatom-containing amines
Transition-metal-free and solvent-free
+
Uses 1.5 equiv of NaOtBu and 3.0 equiv of the N,N-disubstituted amide
R1 NH2neat
S
pecial Topic3286
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https://doi.org/10.1055/s-0040-1705892https://doi.org/10.1055/s-0040-1707146