Reaction of silyl ketene acetals with epoxides: a new method for the synthesis of gamma-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 gamma-haloalkyl-gamma-butanolides thus obtained can be further transformed into various products. (C) 2004 Elsevier Ltd. All rights reserved.
Keywords:
epoxides / ketene acetals / lactones / titanium and compounds / alkylationSource:
Tetrahedron, 2004, 60, 40, 8957-8966Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
DOI: 10.1016/j.tet.2004.07.007
ISSN: 0040-4020