Intramolecular Lewis Acid-Catalyzed Asymmetric Hetero-Diels-Alder Reactions with Dienes Bearing Chiral Sulfinyl Groups.

Abstract A chiral α-sulfinyl α,β-unsaturated ketone served as a chiral diene in intramolecular Lewis acid-catalyzed asymmetric cycloaddition reactions, giving hetero-Diels-Alder reaction products along in some cases with ene reaction products in high optical yields. The reaction pathways for Diels-Alder or ene reactions were readily controlled depending on the Lewis acids used.