Activation Modes in Asymmetric Anion-Binding Catalysis

被引:15
作者
Entgelmeier, Lukas-M [1 ]
Mancheno, Olga Garcia [1 ]
机构
[1] Westfalische Wilhelms Univ Munster, Organ Chem Inst, Corrensstr 36, D-48149 Munster, Germany
来源
SYNTHESIS-STUTTGART | 2022年 / 54卷 / 18期
关键词
anion-binding catalysis; homogeneous asymmetric catalysis; non-covalent interactions; activation modes; STABILIZED BRONSTED ACIDS; KINETIC RESOLUTION; DUAL-CATALYSIS; PI CATALYSIS; BOND DONORS; ENANTIOSELECTIVE DEAROMATIZATION; NUCLEOPHILIC DEAROMATIZATION; STEREOGENIC CENTERS; AMINES; ORGANOCATALYSIS;
D O I
10.1055/a-1846-6139
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Over the past two decades, enantioselective anion-binding catalysis has emerged as a powerful strategy for the induction of chirality in organic transformations. The stereoselectivity is achieved in a range of different reactions by using non-covalent interactions between a chiral catalyst and an ionic substrate or intermediate, and subsequent formation of a chiral contact ion pair upon anion binding. This strategy offers vast possibilities in catalysis and the constant development of new reactions has led to various substrate activation approaches. This review provides an overview on the different activation modes in asymmetric anion-binding catalysis by looking at representative examples and recent advances made in this field.
引用
收藏
页码:3907 / 3927
页数:21
相关论文
共 158 条
[1]   Expanded Chiral Surfaces for Asymmetric Anion- Catalysis [J].
Akamatsu, Masaaki ;
Matile, Stefan .
SYNLETT, 2016, 27 (07) :1041-1046
[2]   THE OLEFIN ALDEHYDE CONDENSATION - THE PRINS REACTION [J].
ARUNDALE, E ;
MIKESKA, LA .
CHEMICAL REVIEWS, 1952, 51 (03) :505-555
[3]   Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis [J].
Banik, Steven M. ;
Levina, Anna ;
Hyde, Alan M. ;
Jacobsen, Eric N. .
SCIENCE, 2017, 358 (6364) :761-764
[4]   Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis [J].
Bendelsmith, Andrew J. ;
Kim, Seohyun Chris ;
Wasa, Masayuki ;
Roche, Stephane P. ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (29) :11414-11419
[5]  
Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/C3SC52265B, 10.1039/c3sc52265b]
[6]   Asymmetric Ion-Pairing Catalysis [J].
Brak, Katrien ;
Jacobsen, Eric N. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :534-561
[7]   σ-Hole Interactions in Catalysis [J].
Breugst, Martin ;
Koenig, Jonas J. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (34) :5473-5487
[8]   STEREOSPECIFIC OLEFIN POLYMERIZATION WITH CHIRAL METALLOCENE CATALYSTS [J].
BRINTZINGER, HH ;
FISCHER, D ;
MULHAUPT, R ;
RIEGER, B ;
WAYMOUTH, RM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (11) :1143-1170
[9]   Enantioselective Catalytic α-Alkylation of Aldehydes via an SN1 Pathway [J].
Brown, Adam R. ;
Kuo, Wen-Hsin ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (27) :9286-9288
[10]   Halogen Bonding in Organic Synthesis and Organocatalysis [J].
Bulfield, David ;
Huber, Stefan M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (41) :14434-14450