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Synfacts 2007(7): 0758-0758  
DOI: 10.1055/s-2007-968633
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Highly Enantio- and Diastereoselective Cascade Double Michael Addition

Contributor(s): Benjamin List, Kristina Zumbansen
L. Zu, H. Li, H. Xie, J. Wang, W. Jiang, Y. Tang, W. Wang*
University of New Mexico, Albuquerque, USA and East China University of Science and Technology, Shanghai, P. R. of China
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

A diastereoselective and enantio­selective cascade double Michael reaction has been developed. This cascade reaction generates three contiguous stereogenic centers along with the formation of two C-C bonds in a one-pot transformation. Products were obtained in high yield (85-95%), good to excellent enantioselectivity (84-99% ee) and good diastereoselectivity (10:1 up to >20:1). Large substituents both on the aldehyde substrate (R) as well as on the ester (R′) are well tolerated without significant influence on the yield.