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Stereoconvergent, Redox‐Neutral Access to Tetrahydroquinoxalines through Relay Epoxide Opening/Amination of Alcohols
Author(s) -
Xu Guangda,
Yang Guoqiang,
Wang Yue,
Shao PanLin,
Yau Jia Ning Nicolette,
Liu Bing,
Zhao Yunbo,
Sun Ye,
Xie Xinxin,
Wang Shuo,
Zhang Yao,
Xia Lixin,
Zhao Yu
Publication year - 2019
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.201906199
Subject(s) - epoxide , catalysis , enantioselective synthesis , redox , reagent , combinatorial chemistry , amination , chemistry , organic chemistry , iridium , reductive amination
We present an economical catalytic procedure to convert readily available 1,2‐diaminobenzenes and terminal epoxides into valuable 1,2,3,4‐tetrahydroquinoxalines in a highly enantioselective fashion. This procedure operates through relay zinc and iridium catalysis, and achieves redox‐neutral and stereoconvergent production of valuable chiral heterocycles from racemic starting materials with water as the only side product. The use of commercially available reagents and catalysts and a convenient procedure also make this catalytic method attractive for practical application.