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Synfacts 2009(5): 0519-0519  
DOI: 10.1055/s-0029-1216616
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Acid-Base-Catalyzed Asymmetric α-Crotylation of Aldehydes

Contributor(s): Hisashi Yamamoto, Pingfan Li
A. V. Malkov*, M. A. Kabeshov, M. Barłog, P. Kočovský*
University of Glasgow and Loughborough University, UK
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Publikationsverlauf

Publikationsdatum:
22. April 2009 (online)

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Significance

Asymmetric α-crotylation of aldehydes is realized via a two-step sequence: first a chiral Lewis base catalyzed anti-selective γ-crotyl­ation with high enantioselectivities, then a Lewis acid catalyzed crotyl transfer with high stereoselectivities. Several products, previously difficult to access, are obtained with over 95% ee. The ­current procedure solves a rather difficult and long-standing problem for this isomerization.