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Synfacts 2008(1): 0095-0095  
DOI: 10.1055/s-2007-991415
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Cascade Michael-Aldol Condensation Reaction

Contributor(s): Benjamin List, Subhas Chandra Pan
J. Wang, H. Li, H. Xie, L. Zu, X. Shen, W. Wang*
University of New Mexico, Albuquerque, USA; East China University of Science & Technology, Shanghai and Shanghai Institute of Materia Medica, P. R. of China
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Publikationsverlauf

Publikationsdatum:
18. Dezember 2007 (online)

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Significance

The authors report an organocatalytic asymmetric Michael-aldol condensation reaction for the generation of chiral cyclopentenes. Diphenyl prolinol trimethyl silyl ether 1 in combination with sodium acetate was found to be the best catalyst system for this reaction. Without the additive the reaction yield was somewhat lower. With 10 mol% of catalyst 1, good yields (63-89%) and excellent enantioselectivities (er = 96:4 to 98:2) are obtained for different α,β-unsaturated aldehydes.