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Highly Enantioselective Conjugate Addition of Thioglycolate to Chalcones Catalyzed by Lanthanum: Low Catalyst Loading and Remarkable Chiral Amplification
Author(s) -
Hui Yonghai,
Jiang Jun,
Wang Wentao,
Chen Weiliang,
Cai Yunfei,
Lin Lili,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2010
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.201000105
Subject(s) - enantioselective synthesis , conjugate , catalysis , lanthanum , yield (engineering) , chemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , mathematics , materials science , mathematical analysis , metallurgy
Ramping it up : The titled reaction has been developed using a chiral N , N ′‐dioxide–La III complex as the catalyst. The reaction proceeded with high yield and enantioselectivity. Remarkably, a high asymmetric amplification was observed, as 98 % ee was achieved using 1 mol % L /La(OTf) 3 in which the ee value of L was 2 % ee. Tf=trifluoromethanesulfonyl.