A Convenient Method for the Preparation of Conjugated Olefins from Allylic Acetates and Aldehydes. Synthesis of Pellitorine

Abstract

A variety of allylic acetates were treated with sodium bromide and triphenylphosphine in the presence of 5 mol% of [Pd(PPh3)4] to give the phosphonium salts, which were converted to the ylids in situ and allowed to react with various aldehydes to afford the corresponding conjugated olefins in good yields. Furthermore, this procedure was applied to the synthesis of an insecticidal substance, Pellitorine.