A SIMPLE SYNTHESIS OF α,β-UNSATURATED ALDEHYDES BY THE REACTION OF VINYLSILANES WITH DICHLOROMETHYL METHYL ETHER PROMOTED BY TITANIUM(IV) CHLORIDE. APPLICATION TO THE SYNTHESIS OF ETHYL 12-OXO-10(<i>E</i>)-DODECENOATE AND NUCIFERAL

Abstract

Abstract 1,2-Disubstituted vinyltrimethylsilanes (1) readily underwent formylation with replacement of the silyl group when treated with dichloromethyl methyl ether and titanium(IV) chloride. This reaction provides a simple procedure for the selective preparation of (E)-2-alkenals (2) and was conveniently applied to the synthesis of ethyl 12-oxo-10(E)-dodecenoate and nuciferal.