Palladium-Catalyzed Intramolecular Metallo-Ene Reactions Using Allylic Sulfones as Enophiles

Abstract

Palladium-catalyzed intramolecular metallo-ene reactions were studied using allylic sulfones as enophiles. Palladium-catalyzed reactions of allylic acetates and methyl carbonates bearing allylic sulfones at appropriate sites were carried out in acetic acid at 80°C to give cyclized products, cyclohexane derivatives, with extremely high diastereoselectivity. The stereochemistry of these reactions was examined under various reaction conditions using several model compounds.