Tetrahedron

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

V Maslak, R Matović, RN Saičić

Index: Maslak, Veselin; Matovic, Radomir; Saicic, Radomir N. Tetrahedron, 2004 , vol. 60, # 40 p. 8957 - 8966

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Citation Number: 26

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.