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Synfacts 2007(8): 0862-0862
DOI: 10.1055/s-2007-968741
DOI: 10.1055/s-2007-968741
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Synthesis of (E)-α,β-Unsaturated Esters from 2,2-Dichloroesters and Aldehydes
J. M. Concellón*, H. Rodríguez-Solla, P. Díaz, R. Llavona
Universidad de Oviedo, Spain
Further Information
Publication History
Publication Date:
24 July 2007 (online)
Significance
Although a vast number of synthetic methods are available for the synthesis of α,β-unsaturated esters from aldehydes, most of them do not offer complete stereoselectivity for the C=C bond formation. Herein, a new interesting protocol for this reaction is presented, which uses 2,2-dichloroesters and active manganese as reducing agent. The process gives exclusively E-isomers, also in the case of α,β-disubstituted acrylates, where the stereocontrol is especially difficult. In many cases, this methodology competes favorably with the conventional Wittig reaction.