Highly diastereo- and enantioselective direct aldol reactions of cycloketones with aldehydes catalyzed by a trans-4-tert-butyldimethylsiloxy-L-proline amide

被引:41
作者
He, Long [1 ]
Jiang, Jun
Tang, Zhuo
Cui, Xin
Mi, Ai-Qiao
Jiang, Yao-Zhong
Gong, Liu-Zhu
机构
[1] China W Normal Univ, Coll Chem & Chem Engn, Nanchong 637002, Peoples R China
[2] Chinese Acad Sci, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China
[3] Chinese Acad Sci, Union Lab Asymmetr Synth, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
[4] Chinese Acad Sci, Grad Sch, Beijing, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.tetasy.2007.01.028
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An organocatalyst derived from trans-4-hydroxy-L-proline and (1S,2S)-1,2-diphenyl-2-aminoethanol catalyzes the direct aldol reactions of cycloketones with. a wide scope of aldehydes in high yields and with excellent diastereoselectivities of up to > 99:1 and enantioselectivities of up to > 99% ee. (c) 2007 Published by Elsevier Ltd.
引用
收藏
页码:265 / 270
页数:6
相关论文
共 37 条
[11]   Highly diastereo- and enantioselective direct aldol reactions in water [J].
Hayashi, Y ;
Sumiya, T ;
Takahashi, J ;
Gotoh, H ;
Urushima, T ;
Shoji, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (06) :958-961
[12]   A highly active 4-siloxyproline catalyst for asymmetric synthesis [J].
Hayashi, Y ;
Yamaguchi, J ;
Hibino, K ;
Sumiya, T ;
Urushima, T ;
Shoji, M ;
Hashizume, D ;
Koshino, H .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (12) :1435-1439
[13]  
JIANG J, 2006, CHEM COMMUN
[14]   Discovery of new peptide-based catalysts for the direct asymmetric aldol reaction [J].
Kofoed, J ;
Nielsen, J ;
Reymond, JL .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (15) :2445-2447
[15]  
LIST, 2000, J AM CHEM SOC, V122, P2395
[16]   Proline-catalyzed asymmetric reactions [J].
List, B .
TETRAHEDRON, 2002, 58 (28) :5573-5590
[17]   Asymmetric aminocatalysis [J].
List, B .
SYNLETT, 2001, (11) :1675-1686
[18]   Enamine catalysis is a powerful strategy for the catalytic generation and use of carbanion equivalents [J].
List, B .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :548-557
[19]   The direct catalytic asymmetric three-component Mannich reaction [J].
List, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9336-9337
[20]  
Martin HJ, 2003, SYNLETT, P1901