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Highly Enantioselective Direct Michael Addition of 1 H ‐Benzotriazole to Chalcones Catalyzed by Sc(OTf) 3 / N , N ′‐Dioxide Complex
Author(s) -
Wang Jing,
Wang Wentao,
Liu Xiaohua,
Hou Zongrui,
Lin Lili,
Feng Xiaoming
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100021
Subject(s) - chemistry , benzotriazole , michael reaction , enantioselective synthesis , catalysis , alcohol , amide , organic chemistry , medicinal chemistry , combinatorial chemistry
The N , N′ ‐dioxide–Sc(OTf) 3 complex was applied in the asymmetric Michael reaction of 1 H ‐benzotriazole with chalcones to give the corresponding N‐1 products in excellent yields (up to 99 %) with excellent enantioselectivities (up to 99 % ee ). Further transformation into other optically active derivatives such as β‐benzotriazolyl ester, alcohol, and amide were also realized with excellent results.