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Synfacts 2006(2): 0176-0176  
DOI: 10.1055/s-2005-921769
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

PS-PEG-Supported Proline Catalysis for Aldol Reaction

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Takayasu Arakawa
K. Akagawa, S. Sakamoto, K. Kudo*
University of Tokyo, Japan
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

The recyclable PS-PEG resin-supported tripeptide catalyst 1 promoting the direct asymmetric aldol reaction of acetone with aldehydes was developed. The direct asymmetric aldol reaction (DAAR) of p-nitrobenzaldehyde with acetone by using catalyst 1 and ZnCl2 was performed at 0 °C to give the aldol product having S-configuration in quantitative yield with 71% ee. Catalyst 1 was reused five times without any loss of its catalytic activity and enantioselectivity (see scheme). Five examples of the aldol reaction of various aldehydes were demonstrated (50-100% yields, 71-84% ee).