Preparation of β,γ-Unsaturated Methyl Esters from Allylic Alcohols

Article abstract of DOI:10.1021/jo01309a013

β,γ-Unsaturated esters are of interest for the synthesis of mono- and sesquiterpenes where the alkene linkage is destined for cleavage to a dialdehyde as well as for the synthesis of γ-butyrolactones. A general method for the preparation of deconjugated esters of this type from allylic alcohols is described. The method is useful for the construction of β,γ-unsaturated esters where the ? bond is disubstituted and part of a cyclic array. The sequence works only poorly in acyclic systems.