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Synfacts 2007(12): 1318-1318  
DOI: 10.1055/s-2007-991333
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Desymmetrization of Meso-Aziridines

Contributor(s): Benjamin List, Frank Lay
E. B. Rowland, G. B. Rowland, E. Rivera-Otero, J. C. Antilla*
University of South Florida, Tampa, USA
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Publication History

Publication Date:
22 November 2007 (online)

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Significance

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.