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Synfacts 2007(8): 0871-0871  
DOI: 10.1055/s-2007-968759
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Tandem Michael-Henry Reaction

Contributor(s): Benjamin List, Daniela Kampen
Y. Hayashi*, T. Okano, S. Aratake, D. Hazelard
Tokyo University of Sciences, Japan
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

An organocatalytic asymmetric tandem reaction for the construction of highly functionalized cyclohexane carbaldehydes is described. Chiral α,α-diphenylprolinol silyl ether 1 (10 mol%) mediates a Michael addition of pentane-1,5-dial (3) to nitroolefins 2 followed by an intra­molecular Henry reaction to give products of type 4 in good yields, diastereoselectivities and excellent enantioselectivities. Two C-C bonds and four stereocenters are generated in the process.