Merrifield Resin Supported Dipeptides: Efficient and Recyclable Organo­catalysts for Asymmetric Aldol Reactions under Neat Reaction Conditions

Jincan Yan; Lei Wang

doi:10.1055/s-2008-1067104

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Synthesis 2008(13): 2065-2072
DOI: 10.1055/s-2008-1067104

PAPER

Merrifield Resin Supported Dipeptides: Efficient and Recyclable Organocatalysts for Asymmetric Aldol Reactions under Neat Reaction Conditions

Jincan Yan^a, Lei Wang*^a,b
^a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

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Publication History

Received 3 March 2008
Publication Date:
21 May 2008 (online)

Abstract
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Abstract

A number of Merrifield resin supported dipeptide and tripeptide catalysts have been developed of which Pro-Ala-O-P, catalyst A, was found to be an efficient catalyst for asymmetric direct aldol reactions. Aldehydes and ketones underwent smooth aldol reaction in the presence of a catalytic amount of A at room temperature under neat reaction conditions and generated the corresponding products with excellent isolated yields (≤98%), good diastereoselectivities (dr ≤ 90:10) and enantioselectivities (≤95% ee). In addition, catalyst A could be used seven times without loss of its catalytic activity.

Key words

Merrifield resin - organocatalyst - aldol reaction - peptide - neat reaction conditions

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