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Synfacts 2011(9): 0974-0974  
DOI: 10.1055/s-0030-1261006
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Synthesis of Substituted Pyrrolidines

Contributor(s): Mark Lautens, Hasnain A. Malik
M. A. Lowe, M. Ostovar, S. Ferrini, C. C. Chen, P. G. Lawrence, F. Fontana, A. A. Calabrese, V. K. Aggarwal*
University of Bristol, UK
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Publication History

Publication Date:
19 August 2011 (online)

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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.