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Highly Enantioselective Direct Michael Addition of Nitroalkanes to Nitroolefins Catalyzed by La(OTf) 3 / N , N ′‐Dioxide Complexes
Author(s) -
Yang Xu,
Zhou Xin,
Lin Lili,
Chang Lu,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2008
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.200802285
Subject(s) - enantioselective synthesis , stereocenter , michael reaction , catalysis , chemistry , content (measure theory) , organic chemistry , combinatorial chemistry , mathematics , mathematical analysis
It all adds up : A chiral La(OTf) 3 / N , N ′‐dioxide complex has been developed for the asymmetric direct Michael addition of nitroalkanes to nitroalkenes. This reaction afford 1,3‐dinitro compounds with two stereocenters in good yields with high diastereo‐ and enantioselectivity (up to d.r. 93:3, 97 % ee ; see scheme, Tf=trifluoromethanesulfonyl) under mild conditions.