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Enantioselective Desymmetrization of meso Epoxides with Anilines Catalyzed by a Niobium Complex of a Chiral Multidentate Binol Derivative
Author(s) -
Arai Kenzo,
Salter Matthew M.,
Yamashita Yasuhiro,
Kobayashi Shū
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200603787
Subject(s) - desymmetrization , stereoselectivity , enantioselective synthesis , denticity , chemistry , catalysis , methoxide , derivative (finance) , ring (chemistry) , lewis acids and bases , niobium , stereochemistry , organic chemistry , metal , financial economics , economics
Molecular recognition in the desymmetrization of meso epoxides with anilines is displayed by a Lewis acid catalyst formed from niobium(V) methoxide and a novel tetradentate binol derivative. The catalyst has a remarkable ability to distinguish between different meso epoxides (see scheme) and also efficiently mediates the ring opening of unsymmetrically disubstituted epoxides with high chemo‐ and stereoselectivity.