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Desymmetrization of Meso-Aziridines
E. B. Rowland, G. B. Rowland, E. Rivera-Otero, J. C. Antilla*
University of South Florida, Tampa, USA
22 November 2007 (online)
This is the first organocatalytic enantioselective ring opening of meso-aziridines. The desymmetrization of aziridines with acyclic, aliphatic, and aryl substituents has been achieved in high yields and with good enantioselectivities by using VAPOL-derived phosphoric acid 1 as catalyst. Preliminary mechanistic studies point to a chiral silylphosphate as the active catalytic species.