Chiral pyrrolidine-triazole conjugate catalyst for asymmetric Michael and Aldol reactions

被引：46

作者：

Chandrasekhar, S. ^{[1
]}

Tiwarl, Bhoopendra ^{[1
]}

Parida, Bibhuti B. ^{[1
]}

Reddy, Ch. Raji ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 04期

关键词：

D O I：

10.1016/j.tetasy.2008.01.033

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new pyrrolidine-triazole conjugate organocatalyst is synthesized using a Huisgen 1,3-dipolar cycloaddition reaction. The application of this catalyst in an asymmetric Michael addition and in an Aldol reaction is described, showing good catalytic activity. The reactions proceeded to give the products in good yield and in a highly selective manner. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：495 / 499

页数：5

共 35 条

[1] Click chemistry as a route to cyclic tetrapeptide analogues:: Synthesis of cyclo-[Pro-Val-Ψ(triazole)-Pro-Tyr] [J].

Bock, VD ;

Perciaccante, R ;

Jansen, TP ;

Hiemstra, H ;

van Maarseveen, JH .

ORGANIC LETTERS, 2006, 8 (05) :919-922

[2] 1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics [J].

Bock, Victoria D. ;

Speijer, Dave ;

Hiemstra, Henk ;

van Maarseveen, Jan H. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (06) :971-975

[3]

Carreira E. M., 1999, COMPREHENSIVE ASYMME, VIII

[4] L-Proline-catalyzed one-pot synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones [J].

Chandrasekhar, S. ;

Vijeender, K. ;

Sridhar, Ch. .

TETRAHEDRON LETTERS, 2007, 48 (28) :4935-4937

[5] Three-component coupling of alkynes, Baylis-Hillman adducts and sodium azide: a new synthesis of substituted triazoles [J].

Chandrasekhar, S ;

Basu, D ;

Rambabu, C .

TETRAHEDRON LETTERS, 2006, 47 (18) :3059-3063

[6] L-Proline catalysed asymmetric aldol reactions in PEG-400 as recyclable medium and transfer aldol reactions [J].

Chandrasekhar, S ;

Reddy, NR ;

Sultana, SS ;

Narsihmulu, C ;

Reddy, KV .

TETRAHEDRON, 2006, 62 (2-3) :338-345

[7] L-proline catalyzed asymmetric transfer aldol reaction between diacetone alcohol and aldehydes [J].

Chandrasekhar, S ;

Narsihmulu, C ;

Reddy, NR ;

Sultana, SS .

CHEMICAL COMMUNICATIONS, 2004, (21) :2450-2451

[8] Inter and intramolecular copper(I)-catalyzed 1,3-dipolar cycloaddition of azido-alkynes: synthesis of furanotriazole macrocycles [J].

Chandrasekhar, Srivari ;

Rao, Chennamaneni Lohitha ;

Nagesh, Chidalla ;

Reddy, Chada Raji ;

Sridhar, Balasubramanian .

TETRAHEDRON LETTERS, 2007, 48 (33) :5869-5872

[9]

Enders D, 2002, SYNLETT, P26

[10]

Fan JF, 2006, CHINESE J ORG CHEM, V26, P1463

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