Effective asymmetric Michael addition of acetone to nitroalkenes promoted by chiral proline amide-thiourea bifunctional catalysts

被引:21
作者
Wang, Qiao-wei [1 ,2 ]
Peng, Lin [1 ,2 ]
Fu, Ji-ya [1 ,2 ]
Huang, Qing-chun
Wang, Li-xin [1 ]
Xu, Xiao-ying [1 ]
机构
[1] Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
基金
中国国家自然科学基金;
关键词
Organocatalyst; Michael addition; acetone; trans-nitroalkenes; chiral proline amidethiourea; ENANTIOSELECTIVE CONJUGATE ADDITION; EFFICIENT ORGANOCATALYSTS; 1,4-ADDITION REACTIONS; PYRROLIDINE-THIOUREA; KETONES; ALDEHYDES; AMINE; NITROOLEFINS; DERIVATIVES; STEREOCENTERS;
D O I
10.3998/ark.5550190.0011.229
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of secondary amine-thiourea catalysts 1a-1d derived from L-proline and chiral diamine were prepared and successfully applied to the Michael addition of acetone to trans-nitroalkenes in excellent yields (up to 99%) and enantioselectivities (44-91% ee).
引用
收藏
页码:340 / 351
页数:12
相关论文
共 75 条
[11]   Construction of quaternary stereocenters: New perspectives through enantioselective Michael reactions [J].
Christoffers, J ;
Baro, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1688-1690
[12]  
Christoffers J, 1998, EUR J ORG CHEM, V1998, P1259
[13]   Small-molecule H-bond donors in asymmetric catalysis [J].
Doyle, Abigail G. ;
Jacobsen, Eric N. .
CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743
[14]  
Enders D, 2002, SYNLETT, P26
[15]   Organocatalytic asymmetric domino reactions:: A cascade consisting of a Michael addition and an aldehyde α-alkylation [J].
Enders, Dieter ;
Wang, Chuan ;
Bats, Jan W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) :7539-7542
[16]   Iminium catalysis [J].
Erkkila, Anniina ;
Majander, Inkeri ;
Pihko, Petri M. .
CHEMICAL REVIEWS, 2007, 107 (12) :5416-5470
[17]   Sugar-derived bifunctional thiourea organocatalyzed asymmetric Michael addition of acetylacetone to nitroolefins [J].
Gao, Peng ;
Wang, Chungui ;
Wu, Yang ;
Zhou, Zhenghong ;
Tang, Chuchi .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (27) :4563-4566
[18]   Highly enantioselective Michael addition of acetone to nitroolefins catalyzed by chiral bifunctional primary amine-thiourea catalysts with acetic acid [J].
Gu, Qing ;
Guo, Xing-Tao ;
Wu, Xin-Yan .
TETRAHEDRON, 2009, 65 (27) :5265-5270
[19]   Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes [J].
Hayashi, Y ;
Gotoh, H ;
Hayashi, T ;
Shoji, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) :4212-4215
[20]   Highly enantioselective direct conjugate addition of ketones to nitroalkenes promoted by a chiral primary amine-thiourea catalyst [J].
Huang, Hongbing ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7170-7171