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Synfacts 2010(7): 0831-0831  
DOI: 10.1055/s-0029-1220122
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Cyclodextrin-Supported Primary Amine Catalyzed Aldol Reaction

Contributor(s): Benjamin List, Ji-Woong Lee
S. Hu, J. Li, J. Xiang, J. Pan, S. Luo*, J.-P. Cheng*
Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. of China
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

The authors present an asymmetric aldol reaction promoted by β-cyclodextrin-supported chiral primary amine 1. Supramolecular recognition of the cyclodextrin moiety generates a synergistic effect on catalytic activity and enantio­selectivity. A slightly acidic environment was found to be optimal for the catalysis. Substrate binding mode and conformational change of the catalyst during the reaction course was confirmed using a sophisticated spectroscopic analysis.