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Synfacts 2009(5): 0519-0519
DOI: 10.1055/s-0029-1216616
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
A. V. Malkov*, M. A. Kabeshov, M. Barłog, P. Kočovský*
University of Glasgow and Loughborough University, UK
Further Information
Publication History
Publication Date:
22 April 2009 (online)
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.