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
[1]   Organocatalytic asymmetric conjugate additions [J].
Almasi, Diana ;
Alonso, Diego A. ;
Najera, Carmen .
TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365
[2]   Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].
Ballini, R ;
Bosica, G ;
Fiorini, D ;
Palmieri, A ;
Petrini, M .
CHEMICAL REVIEWS, 2005, 105 (03) :933-971
[3]   Chiral piperazines as efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes [J].
Barros, Maria Teresa ;
Phillips, Ana Maria Faisca .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (01) :178-185
[4]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[5]   Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].
Betancort, JM ;
Barbas, CF .
ORGANIC LETTERS, 2001, 3 (23) :3737-3740
[6]   Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins [J].
Cao, Chun-Li ;
Ye, Meng-Chun ;
Sun, Xiu-Li ;
Tang, Yong .
ORGANIC LETTERS, 2006, 8 (14) :2901-2904
[7]   Michael additions in water of ketones to nitroolefins catalyzed by readily tunable and bifunctional pyrrolidine-thiourea organocatalysts [J].
Cao, Yi-Ju ;
Lai, Yuan-Yuan ;
Wang, Xiang ;
Li, Yong-Han ;
Xiao, Wen-Jing .
TETRAHEDRON LETTERS, 2007, 48 (01) :21-24
[8]   Preparation the key intermediate of angiotensin-converting enzyme (ACE) inhibitors:: High enantioselective production of ethyl (R)-2-hydroxy-4-phenylbutyrate with Candida boidinii CIOC21 [J].
Chen, Yongzheng ;
Lin, Hui ;
Xu, Xiaoying ;
Xia, Shiwen ;
Wang, Lixin .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :426-430
[9]   Enantiocomplementary preparation of (S)- and (R)-mandelic acid derivatives via α-hydroxylation of 2-arylacetic acid derivatives and reduction of α-ketoester using microbial whole cells [J].
Chen, Yongzheng ;
Xu, Jinggang ;
Xu, Xiaoying ;
Xia, Yu ;
Lin, Hui ;
Xia, Shiwen ;
Wang, Lixin .
TETRAHEDRON-ASYMMETRY, 2007, 18 (21) :2537-2540
[10]   Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene:: Efficient access to γ2-amino acids [J].
Chi, Yonggui ;
Guo, Li ;
Kopf, Nathan A. ;
Gellman, Samuel H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5608-+