Highly enantioselective aldol reactions catalyzed by a recyclable fluorous (S) pyrrolidine sulfonamide on water

被引：126

作者：

Zu, Liansuo ^{[1
]}

Xie, Hexin ^{[1
]}

Li, Hao ^{[1
]}

Wang, Jian ^{[1
]}

Wang, Wei ^{[1
]}

机构：

[1] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 06期

关键词：

D O I：

10.1021/ol800074z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorous (S) pyrrolidine sulfonamide serves as an efficient promoter for highly enantioselective aldol reactions of ketones and aldehydes with aromatic aldehydes on water. A notable feature of the organocatalyst is that it can be recovered from the reaction mixtures by simple fluorous solid-phase extraction and subsequently reused (up to seven cycles) without a significant loss of catalytic activity and stereoselectivity.

引用

页码：1211 / 1214

页数：4

共 62 条

[1] Highly enantioselective Michael additions in water catalyzed by a PS-Supported pyrrolidine [J].

Alza, Esther ;

Cambeiro, Xacobe C. ;

Jimeno, Ciril ;

Pericas, Miquel A. .

ORGANIC LETTERS, 2007, 9 (19) :3717-3720

[2]

[Anonymous], ACC CHEM RES

[3] Small organic molecule in enantioselective, direct aldol reaction "in water'' [J].

Aratake, Seiji ;

Itoh, Takahiko ;

Okano, Tsubasa ;

Usui, Takahiro ;

Shoji, Mitsuru ;

Hayashi, Yujiro .

CHEMICAL COMMUNICATIONS, 2007, (24) :2524-2526

[4]

BARBARA P, 2007, CHEM COMMUN, P1421

[5]

Benaglia M, 2001, ADV SYNTH CATAL, V343, P171, DOI 10.1002/1615-4169(20010226)343:2<171::AID-ADSC171>3.3.CO

[6]

2-V

[7]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[8] Water in organocatalytic processes: Debunking the myths [J].

Blackmond, Donna G. ;

Armstrong, Alan ;

Coombe, Vyv ;

Wells, Andrew .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3798-3800

[9] Enamine-based aldol organocatalysis in water: Are they really "all wet"? [J].

Brogan, Andrew P. ;

Dickerson, Tobin J. ;

Janda, Kim D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (48) :8100-8102

[10] 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

← 1 2 3 4 5 6 7 →