(S)-Pyrrolidine sulfonamide catalyzed asymmetric direct aldol reactions of aryl methyl ketones with aryl aldehydes

被引：57

作者：

Mei, Kui ^{[1
]}

Zhang, Shilel ^{[1
]}

He, Songtao ^{[2
]}

Li, Ping ^{[1
]}

Jin, Mel ^{[1
]}

Xue, Fei ^{[1
]}

Luo, Guangshun ^{[1
]}

Zhang, Haoyi ^{[1
]}

Song, Lirong ^{[1
]}

Duan, Wenhu ^{[1
,2
]}

Wang, Wei ^{[1
,3
]}

机构：

[1] E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Sci, Shanghai 200237, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai Inst Biol Sci, Grad Sch, Shanghai 201203, Peoples R China

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

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 17期

关键词：

aldol reaction; aryl alkyl ketones; pyrrolidine sulfonamide;

D O I：

10.1016/j.tetlet.2008.02.164

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A (S)-pyrrolidine sulfonamide catalyzed asymmetric direct aldol reaction of aryl methyl ketones with aromatic aldehydes has been developed with moderate to good enantioselectivities. The study considerably broadens the substrate scope of chiral amines promoted aldol processes. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2681 / 2684

页数：4

共 74 条

[1] Recent progress in chiral Bronsted acid catalysis [J].

Akiyama, Takahiko ;

Itoh, Junji ;

Fuchibe, Kohei .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010

[2]

AO CL, 2007, J ORG CHEM, V72, P4073

[3] 4-Substituted prolines as organocatalysts for aldol reactions [J].

Bellis, E ;

Kokotos, G .

TETRAHEDRON, 2005, 61 (36) :8669-8676

[4] 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

[5] Enantioselective formal [3+3] annulation for the direct construction of bicyclic skeletons with four stereogenic Centers [J].

Cao, Chun-Li ;

Sun, Xiu-Li ;

Kang, Yan-Biao ;

Tang, Yong .

ORGANIC LETTERS, 2007, 9 (21) :4151-4154

[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] Readily tunable and bifunctional L-prolinamide derivatives: Design and application in the direct enantioselective aldol reactions [J].

Chen, JR ;

Lu, HH ;

Li, XY ;

Cheng, L ;

Wan, J ;

Xiao, WJ .

ORGANIC LETTERS, 2005, 7 (20) :4543-4545

[8] Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: Beneficial effects of hydrogen bonding [J].

Chen, Wei ;

Du, Wei ;

Duan, Yong-Zheng ;

Wu, Yong ;

Yang, Sheng-Yong ;

Chen, Ying-Chun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7667-7670

[9] Protonated N′-benzyl-N′-prolyl proline hydrazide as highly enantioselective catalyst for direct asymmetric aldol reaction [J].

Cheng, CL ;

Sun, J ;

Wang, C ;

Zhang, Y ;

Wei, SY ;

Jiang, F ;

Wu, YD .

CHEMICAL COMMUNICATIONS, 2006, (02) :215-217

[10] Protonated chiral prolinamide catalyzed enantioselective direct aldol reaction in water [J].

Chimni, SS ;

Mahajan, D ;

Babu, VVS .

TETRAHEDRON LETTERS, 2005, 46 (34) :5617-5619

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