Reaction of silyl ketene acetals with epoxides: A new method for the synthesis of γ-butanolides

Abstract

Titanium tetrachloride promoted reaction of silyl ketene acetals with epoxides, followed by acidic work-up, affords butanolides in moderate/good yields. With epihalohydrins the reaction is regioselective and occurs at the less substituted end of the epoxide; the γ-haloalkyl-γ-butanolides thus obtained can be further transformed into various products. Graphical Abstract © 2004 Elsevier Ltd. All rights reserved.