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A Flexible, Stereoselective Dimethylzinc-Mediated Radical-Anionic Cascade: Dramatic Influence of Additional Lewis Acids
Journal article   Peer reviewed

A Flexible, Stereoselective Dimethylzinc-Mediated Radical-Anionic Cascade: Dramatic Influence of Additional Lewis Acids

Julien Maury, Laurence Feray, Patricia Perfetti and Michèle P. Bertrand
Organic Letters, Vol.12(16), pp.3590--3593
08/2010

Abstract

Dimethylzinc-mediated addition of acyloxymethyl radicals to diethyl fumarate led to the highly stereoselective formation of disubstituted gamma-lactones in mean to good yields; this cascade provides a new example of a one-pot process mediated by dimethylzinc involving a tandem radical-anionic reaction; the chemoselectivity of the reaction was totally modified by additional Lewis acids.
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