Proline-catalyzed asymmetric direct aldol reaction assisted by D-camphorsulfonic acid in aqueous media

被引:67
作者
Wu, YS
Chen, Y
Deng, DS
Cai, JW [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Peoples R China
[2] Hebei Normal Univ, Chem Coll, Shijiazhuang 050016, Peoples R China
关键词
asymmetric direct aldol reaction; co-catalyst; proline; camphorsulfonic acid; aqueous media;
D O I
10.1055/s-2005-869864
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric aldol reactions of aromatic aldehydes with various ketones catalyzed by L-proline with D-camphorsulfonic acid as co-catalyst have been developed in aqueous media. High reactivity and modest to excellent enantioselectivity has been achieved.
引用
收藏
页码:1627 / 1629
页数:3
相关论文
共 29 条
[1]   Proline-derived N-sullfonylcarboxamides:: Readily available, highly enantioselective and versatile catalysts for direct aldol reactions [J].
Berkessel, A ;
Koch, B ;
Lex, J .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1141-1146
[2]   Asymmetric aldol reactions in poly(ethylene glycol) catalyzed by L-proline [J].
Chandrasekhar, S ;
Narsihmulu, C ;
Reddy, NR ;
Sultana, SS .
TETRAHEDRON LETTERS, 2004, 45 (23) :4581-4582
[3]   Direct organocatalytic aldol reactions in buffered aqueous media [J].
Córdova, A ;
Notz, W ;
Barbas, CF .
CHEMICAL COMMUNICATIONS, 2002, (24) :3024-3025
[4]   Zn-proline catalyzed direct aldol reaction in aqueous media [J].
Darbre, T ;
Machuqueiro, M .
CHEMICAL COMMUNICATIONS, 2003, (09) :1090-1091
[5]   Rational design of asymmetric organocatalysts - increased reactivity and solvent scope with a tetrazolic acid [J].
Hartikka, A ;
Arvidsson, PI .
TETRAHEDRON-ASYMMETRY, 2004, 15 (12) :1831-1834
[6]   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
[7]   Application of high pressure, induced by water freezing, to the direct asymmetric aldol reaction [J].
Hayashi, Y ;
Tsuboi, W ;
Shoji, M ;
Suzuki, N .
TETRAHEDRON LETTERS, 2004, 45 (22) :4353-4356
[8]   Proline-catalysed asymmetric aldol reaction in the room temperature ionic liquid [bmim]PF6 [J].
Kotrusz, P ;
Kmentová, I ;
Gotov, B ;
Toma, S ;
Solcániová, E .
CHEMICAL COMMUNICATIONS, 2002, (21) :2510-2511
[9]   Proline-catalyzed asymmetric reactions [J].
List, B .
TETRAHEDRON, 2002, 58 (28) :5573-5590
[10]   Proline-catalyzed direct asymmetric aldol reactions [J].
List, B ;
Lerner, RA ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2395-2396