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Chiral N,N′ ‐Dioxide‐Zinc(II) Complex‐Catalyzed Asymmetric Aza‐Friedel–Crafts Reaction of Isatin‐Derived Ketimines with Indoles
Author(s) -
Zhang Xiying,
Zhang Jianlin,
Lin Lili,
Zheng Haifeng,
Wu Wangbin,
Liu Xiaohua,
Feng Xiaoming
Publication year - 2016
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.201600630
Subject(s) - chemistry , isatin , stereocenter , enantioselective synthesis , friedel–crafts reaction , catalysis , yield (engineering) , zinc , indole test , organic chemistry , medicinal chemistry , combinatorial chemistry , materials science , metallurgy
A highly efficient chiral N,N′ ‐dioxide‐zinc(II) complex catalytic system has been developed for the enantioselective aza‐Friedel–Crafts reaction of isatin‐derived ketimines with indoles. A series of enantiomerically enriched 3‐indolyl‐3‐aminooxindoles containing a tetrasubstituted stereocenter were obtained in up to 99% yield with up to 96% ee . Furthermore, control experiments provide a fundamental sight into the mechanism of the reaction.