Synthesis of (Z)-homoallylic alcohols and homoprop-2-ynylic alcohols via palladium-catalysed hydrogenolysis of prop-2-ynylic cyclic carbonates

Abstract

The decarboxylation–hydrogenolysis of prop-2-ynylic cyclic carbonates which have an internal acetylenic bond with ammonium formate in the presence of a catalytic amount of [Pd(acac)₂] and Buⁿ₃P afforded (Z)-homoallylic alcohols or homoprop-2-ynylic alcohols depending on the reaction conditions, however, hydrogenolysis of terminal prop-2-ynylic cyclic carbonates gave homoallylic alcohols; using (Z)-homoallylic alcohol 2b as a chiral synthon, the male sex pheromone of the pyralid moth Aphomia gularis has been synthesized.