Stereoselective Synthesis of <i>cis-</i>2,5-Disubstituted Pyrrolidines via Wacker-Type Aerobic Oxidative Cyclization of Alkenes with <i>tert</i>-Butanesulfinamide Nucleophiles

Abstract

Palladium(II)-catalyzed aerobic oxidative cyclization of alkenes with tethered tert-butanesulfinamides furnishes enantiopure 2,5-disubstituted pyrrolidines, originating from readily available and easily diversified starting materials. These reactions are the first reported examples of metal-catalyzed addition of sulfinamide nucleophiles to alkenes.