SYNTHESIS OF (Z)-HOMOALLYLIC ALCOHOLS AND HOMOPROP-2-YNYLIC ALCOHOLS VIA PALLADIUM-CATALYZED HYDROGENOLYSIS OF PROP-2-YNYLIC CYCLIC CARBONATES

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)l and Bu(3)(n)P 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 ass chiral synthon, the male sex pheromone of the pyralid moth Aphomia gularis has been synthesized.