Hydroxyphthalimide allied triazole-pyrrolidine catalyst for asymmetric Michael additions in water

被引：32

作者：

Chandrasekhar, Srivari ^{[1
]}

Kumar, Togapur Pavan ^{[1
]}

Haribabu, Kothapalli ^{[1
]}

Reddy, Chada Raji ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 19期

关键词：

ENANTIOSELECTIVE CONJUGATE ADDITION; BETA-NITROSTYRENES; NITRO-MICHAEL; EFFICIENT ORGANOCATALYSTS; RECYCLABLE ORGANOCATALYST; CLICK CHEMISTRY; ALDOL REACTIONS; IONIC LIQUIDS; KETONES; ALDEHYDES;

D O I：

10.1016/j.tetasy.2010.08.012

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new hydroxyphthalimide-coupled triazole-pyrrolidine derivative has been synthesized and demonstrated as an efficient and stereoselective organocatalyst for the asymmetric Michael addition reaction of ketones to nitro olefins at room temperature. Good yields and high selectivities were achieved when benzoic acid was used in combination with organocatalyst 1, employing water as the reaction medium. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2372 / 2375

页数：4

共 81 条

[1] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].

Alexakis, A ;

Andrey, O .

ORGANIC LETTERS, 2002, 4 (21) :3611-3614

[2] Asymmetric conjugate addition of ketones to β-nitrostyrenes by means of 1,2-amino-alcohol-derived prolinamides as bifunctional catalysts [J].

Almasi, Diana ;

Alonso, Diego A. ;

Gomez-Bengoa, Enrique ;

Nagel, Yvonne ;

Najera, Carmen .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (14) :2328-2343

[3] Organocatalytic asymmetric conjugate additions [J].

Almasi, Diana ;

Alonso, Diego A. ;

Najera, Carmen .

TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365

[4] 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

[5] The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins [J].

Andrey, O ;

Alexakis, A ;

Tomassini, A ;

Bernardinelli, G .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1147-1168

[6] Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].

Andrey, O ;

Alexakis, A ;

Bernardinelli, G .

ORGANIC LETTERS, 2003, 5 (14) :2559-2561

[7] Conjugate additions of nitroalkanes to electron-poor alkenes: Recent results [J].

Ballini, R ;

Bosica, G ;

Fiorini, D ;

Palmieri, A ;

Petrini, M .

CHEMICAL REVIEWS, 2005, 105 (03) :933-971

[8]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[9] Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Tanaka, F ;

Barbas, CF .

SYNTHESIS-STUTTGART, 2004, (09) :1509-1521

[10] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].

Betancort, JM ;

Barbas, CF .

ORGANIC LETTERS, 2001, 3 (23) :3737-3740

← 1 2 3 4 5 6 7 8 9 →