Studies on Chiral Organosulfur Compounds. V. Palladium-Catalyzed Intramolecular Asymmetric Metallo-Ene Reactions via Chiral Allylic Sulfinate-Sulfone Rearrangements

Abstract

A palladium-catalyzed intramolecular asymmetric metallo-ene reaction was accomplished using a chiral allylic sulfone (prepared by thermal rearrangement of an optically active allylic sulfinate) as an enophile. The stereoselectivity of the reaction was determined by high-performance liquid chromatography with a chiral column. A plausible mechanistic pathway for this asymmetric cyclization is presented.