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Synfacts 2005(3): 0322-0322  
DOI: 10.1055/s-2005-916128
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Gd(III)-Catalyzed Desymmetrization of Aziridines

Contributor(s): Mark Lautens, Andrew Martins
T. Mita, I. Fujimori, R. Wada, J. Wen, M. Kanai*, M. Shibasaki*
University of Tokyo, Japan
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Publikationsdatum:
22. November 2005 (online)

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Significance

The catalytic, enantioselective ring opening of meso-aziridines is difficult considering the unreactive nature and problematic enantiofacial discrimination associated with these substrates. This method, utilizing an in situ formed dinuclear Gd(III) complex and TMSCN as nucleophile generates enantioenriched trans-β-cyanoamines in excellent yields and enantiomeric excesses from a variety of meso-N-acylaziridines.