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Cinchona Alkaloid Amides/Dialkylzinc Catalyzed Enantioselective Desymmetrization of Aziridines with Phosphites

Author:
Hayashi, Masashi, Shiomi, Noriyuki, Funahashi, Yasuhiro, Nakamura, Shuichi
Source:
Journal of the American Chemical Society 2012 v.134 no.47 pp. 19366-19369
ISSN:
1520-5126
Subject:
Cinchona, alkaloids, amides, catalysts, electrospray ionization mass spectrometry, enantiomers
Abstract:
The first highly enantioselective desymmetrization of aziridines with phosphites has been developed. Excellent yields and enantioselectivities were observed for the reaction with various aziridines using a new class of readily accessible chiral catalysts derived from 9-amino-9-deoxy-epi-cinchona alkaloids. In studies probing the reaction mechanism, we observed some complexes for the cinchona alkaloid amide-Zn(II) by ESI-MS analysis.
Agid:
5387274