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Catalytic Asymmetric Epoxidation of Electron‐Deficient Enynes Promoted by Chiral N,N′ ‐Dioxide‐Scandium(III) Complex
Author(s) -
Zhang Hang,
Yao Qian,
Lin Lili,
Xu Chaoran,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700555
Subject(s) - chemistry , scandium , catalysis , hydrogen peroxide , aqueous solution , enantioselective synthesis , combinatorial chemistry , medicinal chemistry , organic chemistry
An asymmetric epoxidation of electron‐deficient enynes with environmentally benign aqueous hydrogen peroxide as oxidant has been accomplished by developing a chiral N,N′ ‐dioxide‐Scandium(III) complex catalytic system. In the presence of 0.5–2 mol% catalyst, a variety of trisubstituted alkynyl oxiranes were obtained in high yields (up to 97%) with excellent ee values (up to 99%). Furthermore, control experiments provide a fundamental insight into the reaction mechanism.
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