Proline catalyzed aldol reactions in aqueous micelles: an environmentally friendly reaction system

被引:128
作者
Peng, YY
Ding, QP
Li, ZC
Wang, PG
Cheng, JP [1 ]
机构
[1] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China
[2] Jiangxi Normal Univ, Dept Chem, Nanchang 330027, Peoples R China
[3] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0040-4039(03)00692-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The proline catalyzed aldol reactions of nitrobenzaldehydes with various ketones in aqueous anionic micelles were investigated. Both the selectivities and reaction yields were observed to be higher than those of the corresponding reactions in organic solvents. A reaction mechanism is proposed that is somewhat different from that in organic solvents. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3871 / 3875
页数:5
相关论文
共 36 条
[1]  
Agami C., 1988, B SOC CHIM FR MAY, V3, P499
[2]  
Benaglia M, 2001, ADV SYNTH CATAL, V343, P171, DOI 10.1002/1615-4169(20010226)343:2<171::AID-ADSC171>3.3.CO
[3]  
2-V
[4]   CONTROL OF THE AQUEOUS ALDOL ADDITION UNDER CLAISEN-SCHMIDT CONDITIONS [J].
BUONORA, PT ;
ROSAUER, KG ;
DAI, LJ .
TETRAHEDRON LETTERS, 1995, 36 (23) :4009-4012
[5]   Direct organocatalytic aldol reactions in buffered aqueous media [J].
Córdova, A ;
Notz, W ;
Barbas, CF .
CHEMICAL COMMUNICATIONS, 2002, (24) :3024-3025
[6]   Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde [J].
Córdova, A ;
Notz, W ;
Barbas, CF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :301-303
[7]   A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].
Córdova, A ;
Watanabe, S ;
Tanaka, F ;
Notz, W ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867
[8]   A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].
Córdova, A ;
Notz, W ;
Zhong, GF ;
Betancort, JM ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843
[9]   Aqueous aldol catalysis by a nicotine metabolite [J].
Dickerson, TJ ;
Janda, KD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (13) :3220-3221
[10]   TOTAL SYNTHESIS OF OPTICALLY ACTIVE STEROIDS .6. NEW TYPE OF ASYMMETRIC CYCLIZATION TO OPTICALLY ACTIVE STEROID CD PARTIAL STRUCTURES [J].
EDER, U ;
SAUER, G ;
WEICHERT, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (07) :496-&