Pd(0)-Catalyzed Hydrogenolysis of Allylic and Dienylic Cyclic Carbonates: Synthesis of Optically Active Homoallylic Alcohols and Allylic Alcohols

Abstract

Treatment of chiral allylic cyclic carbonates with ammonium formate in the presence of Pd(0) catalyst afforded optically active homoallylic alcohols with excellent regioselectivity. However, hydrogenolysis of dienylic cyclic carbonates in the presence of Pd(0) catalyst afforded conjugated or nonconjugated (E)-dienylic alcohols depending on Pd complexes used. Using homoallylic alcohol 3c as a chiral synthon, (R)-(+)-eldanolide, the sex pheromone of the African sugarcane stem borer, Eldana saccharina, was synthesized.