Synfacts 2007(11): 1207-1207  
DOI: 10.1055/s-2007-991241
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Conjugate Addition of Aldehydes to Vinyl Phosphonates

Contributor(s): Benjamin List, Kristina Zumbansen
S. Sulzer-Mossé, M. Tissot, A. Alexakis*
Université de GenÈve, Switzerland
Further Information

Publication History

Publication Date:
24 October 2007 (online)

Significance

The first organocatalytic enantio­selective conjugate addition of aldehydes to vinyl phosphonates is reported. The corresponding γ-gem-phosphonate aldehydes were obtained in good yields and with high stereoselectivities (85% yield, er = 82.5:17.5 - 98.5:1.5) by using a Hayashi-Jørgensen-type catalyst. The general scope of this reaction is illustrated by employing branched as well as linear aldehydes. The addition products were converted into β-substituted vinyl phosphonates without loss of enantioselectivity. A transition-state model is proposed to rationalize the observed ­stereoselectivity.