Recent Developments in the Synthesis of Chiral Compounds with Quaternary Centers by Organocatalytic Cascade Reactions

被引:80
作者
Tian, Li [1 ]
Luo, Yong-Chun [1 ]
Hu, Xiu-Qin [1 ]
Xu, Peng-Fei [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China
关键词
aminocatalysis; catalytic cascade reactions; hydrogen-bonding catalysis; ion-pairing catalysis; quaternary centers; DIELS-ALDER REACTION; ASYMMETRIC STRECKER REACTION; 4 CONTIGUOUS STEREOCENTERS; PHASE-TRANSFER CATALYSIS; MICHAEL-MICHAEL CASCADE; ENANTIOSELECTIVE CONSTRUCTION; DOMINO REACTIONS; ALPHA; BETA-UNSATURATED KETONES; SPIROOXINDOLE DERIVATIVES; ORGANOCASCADE CATALYSIS;
D O I
10.1002/ajoc.201500486
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Quaternary carbon stereocenters are present in a wide variety of organic compounds and drug molecules. Highly enantioselective construction of such quaternary carbon stereocenters has received considerable attention owing to the great challenges in their syntheses. With the development of asymmetric organocatalytic cascade reactions, several efficient methods for the construction of optically pure compounds with quaternary carbon centers have been developed. This focused review highlights the asymmetric synthesis of chiral compounds with quaternary centers through organocatalytic cascade reactions.
引用
收藏
页码:580 / 607
页数:28
相关论文
共 125 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]   Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].
Akiyama, T ;
Itoh, J ;
Yokota, K ;
Fuchibe, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568
[3]   Assembly of Spirooxindole Derivatives via Organocatalytic Iminium-Enamine Cascade Reactions [J].
Albertshofer, Klaus ;
Anderson, Kimberly E. ;
Barbas, Carlos F., III .
ORGANIC LETTERS, 2012, 14 (23) :5968-5971
[4]   Assembly of Spirooxindole Derivatives Containing Four Consecutive Stereocenters via Organocatalytic Michael-Henry Cascade Reactions [J].
Albertshofer, Klaus ;
Tan, Bin ;
Barbas, Carlos F., III .
ORGANIC LETTERS, 2012, 14 (07) :1834-1837
[5]  
Albrecht L., 2012, ANGEW CHEM, V124, P9222
[6]   Hydrogen-Bonding in Aminocatalysis: From Proline and Beyond [J].
Albrecht, Lukasz ;
Jiang, Hao ;
Jorgensen, Karl Anker .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (02) :358-368
[7]   Enantioselective H-Bond-Directing Approach for Trienamine-mediated Reactions in Asymmetric Synthesis [J].
Albrecht, Lukasz ;
Acosta, Fabio Cruz ;
Fraile, Alberto ;
Albrecht, Anna ;
Christensen, Jannie ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :9088-9092
[8]  
[Anonymous], 2013, ANGEW CHEM
[9]  
[Anonymous], 2012, Angew. Chem, DOI DOI 10.1002/ANGE.201202392
[10]  
[Anonymous], 2012, ANGEW CHEM-GER EDIT