Palladium-Catalyzed Synthesis of Substituted Pyrrolidines

Significance

The stereocontrolled synthesis of complex products from simple and readily accessible starting materials is a longstanding challenge of synthetic organic chemistry. The authors report a diastereoselective palladium-catalyzed annulation of vinyl aziridines with Michael acceptors for the synthesis of substituted pyrrolidines. A steric model is proposed that rationalizes the diastereoselectivity observed. This method is further applied towards an elegant and concise (formal) synthesis of (-)-α-kainic acid.