Asymmetric Friedel-Crafts reaction of indoles with imines by an organic catalyst

被引：300

作者：

Wang, Yong-Qiang ^{[1
]}

Song, Jun ^{[1
]}

Hong, Ran ^{[1
]}

Li, Hongming ^{[1
]}

Deng, Li ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 25期

关键词：

D O I：

10.1021/ja062700v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this communication, we report an asymmetric Friedel-Crafts reaction of indoles with imines catalyzed by a bifunctional cinchona alkaloid catalyst. This is the first efficient organocatalytic asymmetric Friedel-Crafts reaction of indoles with imines. This reaction is operationally simple and, unprecedentedly, affords high enantioselectivity for a wide range of indoles and both aryl and alkyl imines. This establishes a direct, convergent, and versatile approach to optically active 3-indolyl methanamines, a structural motif embedded in numerous indole alkaloids and synthetic indole derivatives. Copyright © 2006 American Chemical Society.

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页码：8156 / 8157

页数：2

相关论文

共 41 条

[31] Highly enantioselective catalytic acyl-Pictet-Spengler reactions [J].

Taylor, MS ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (34) :10558-10559

[32] Asymmetric catalysis by chiral hydrogen-bond donors [J].

Taylor, MS ;

Jacobsen, EN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) :1520-1543

[33] Direct enantio- and diastereoselective Mannich reactions of malonate and β-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivative [J].

Tillman, AL ;

Ye, JX ;

Dixon, DJ .

CHEMICAL COMMUNICATIONS, 2006, (11) :1191-1193

[34] Highly enantioselective organocatalytic hydroxyalkylation of indoles with ethyl trifluoropyruvate [J].

Török, B ;

Abid, M ;

London, G ;

Esquibel, J ;

Török, M ;

Mhadgut, SC ;

Yan, P ;

Prakash, GKS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (20) :3086-3089

[35] Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan [J].

Uraguchi, D ;

Sorimachi, K ;

Terada, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (38) :11804-11805

[36] Structure-based analysis and optimization of a highly enantioselective catalyst for the Strecker reaction [J].

Vachal, P ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) :10012-10014

[37] Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts [J].

Vakulya, B ;

Varga, S ;

Csámpai, A ;

Soós, T .

ORGANIC LETTERS, 2005, 7 (10) :1967-1969

[38] Dual-function cinchona alkaloid catalysis: Catalytic asymmetric tandem conjugate addition-protonation for the direct creation of nonadjacent stereocenters [J].

Wang, Y ;

Liu, XF ;

Deng, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :3928-3930

[39] Construction of quaternary stereocenters by efficient and practical conjugate additions to α,β-unsaturated ketones with a chiral organic catalyst [J].

Wu, FH ;

Li, HM ;

Hong, R ;

Deng, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (06) :947-950

[40] Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives [J].

Ye, JX ;

Dixon, DJ ;

Hynes, PS .

CHEMICAL COMMUNICATIONS, 2005, (35) :4481-4483

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