Recent Progress in (Dynamic) Kinetic Resolution Catalyzed by N-Heterocyclic Carbenes

被引:37
作者
Chen, Shihao [1 ]
Shi, Yu-Hua [2 ]
Wang, Ming [1 ]
机构
[1] East China Normal Univ, Sch Chem & Mol Engn, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
[2] Haimen Molbern Pharmaceut Co Ltd, Haimen Inst Technol, 100 Dongtinghu Rd, Haimen 226000, Peoples R China
基金
美国国家科学基金会;
关键词
alcohols; carbenes; kinetic resolution; organocatalysis; synthetic methods; SECONDARY ALCOHOLS; ASYMMETRIC-SYNTHESIS; ORGANOCATALYSIS; ACYLATION; ESTERS; ACTIVATION; AMINES;
D O I
10.1002/asia.201800537
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic kinetic resolution is often the method of choice for the preparation of optically enriched functionalized compounds and, over the past decade, kinetic resolutions and dynamic kinetic resolutions catalyzed by N-heterocyclic carbenes (NHCs) have been employed for the synthesis of a variety of optically enriched functionalized molecules. Herein we provide an overview of reported NHC-catalyzed kinetic resolutions in terms of the structure of the substrate, the reaction type, and the activation mode. This Focus Review is arranged according to the structure of the racemic compounds and includes the kinetic resolution of alcohols, amines, imines, and aldehydes, as well as dynamic kinetic resolution. In each section, the activation mode and reaction mechanism are discussed. We conclude with a summary of the current state-of-play in NHC-catalyzed kinetic resolution and provide an outlook for the development of this field in the future.
引用
收藏
页码:2184 / 2194
页数:11
相关论文
共 57 条
[1]  
[Anonymous], 2016, ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANGE.201508205
[2]  
[Anonymous], 2012, ANGEW CHE
[3]  
[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[4]  
[Anonymous], 2015, ANGEW CHEM-GER EDIT, DOI DOI 10.1002/ANIE.201303903
[5]   Catalytic Kinetic Resolution of Cyclic Secondary Amines [J].
Binanzer, Michael ;
Hsieh, Sheng-Ying ;
Bode, Jeffrey W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19698-19701
[6]   Atroposelective synthesis of axially chiral biaryl compounds [J].
Bringmann, G ;
Mortimer, AJP ;
Keller, PA ;
Gresser, MJ ;
Garner, J ;
Breuning, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427
[7]  
Bringmann G., 2005, ANGEW CHEM INT EDIT, V117, P5518, DOI 10.1002/ange.200462661
[8]  
Chauhan P., 2014, Angew. Chem. Int. Ed, V126, P1509
[9]   N-Heterocyclic Carbene Catalyzed Activation of Esters: A New Option for Asymmetric Domino Reactions [J].
Chauhan, Pankaj ;
Enders, Dieter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) :1485-1487
[10]  
Chen X. Y., 2018, ANGEW CHEM, V130, P3924