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Synthesis 2008(13): 2065-2072
DOI: 10.1055/s-2008-1067104
DOI: 10.1055/s-2008-1067104
PAPER
© Georg Thieme Verlag Stuttgart · New York
Merrifield Resin Supported Dipeptides: Efficient and Recyclable Organocatalysts for Asymmetric Aldol Reactions under Neat Reaction Conditions
Further Information
Received
3 March 2008
Publication Date:
21 May 2008 (online)
Publication History
Publication Date:
21 May 2008 (online)
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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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