A Stereoselective 1,3-Transposition Reaction of Allylic Alcohols

Abstract

Abstract Reduction of glycidyl mesylate with dissolving metal produces allylic alcohol in fair to excellent yield. Combined with the highly stereoselective epoxidation of allylic alcohols with t-butyl hydroperoxide and oxobis(2,4-pentanedionato-O,O′)vanadium(IV) as a catalyst, the sequence provides a new and efficient means for 1,3-trans-position of allylic alcohols, by which geraniol is transformed into linalool, farnesol into nerolidol, and furthermore, (−)-cis-carveol into the (+) antipode and vice versa in a stereospecific way.