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Iridium‐Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy
Author(s) -
Wang Ye,
Zheng Chao,
You ShuLi
Publication year - 2017
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.201708419
Subject(s) - desymmetrization , stereocenter , allylic rearrangement , iridium , ring (chemistry) , catalysis , enantioselective synthesis , yield (engineering) , chemistry , indole test , stereochemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
A desymmetrization strategy was developed involving iridium‐catalyzed allylic dearomatization of indoles. The six‐membered‐ring spiroindolenines contain three contiguous stereogenic centers, including an all‐carbon quaternary center, and were obtained in up to 99 % yield with 99 % ee and >95:5 d.r. When treated with a catalytic amount of tosylic acid, six‐membered spiroindolenine undergoes an unprecedented six‐to‐seven‐membered ring expansion, affording the corresponding hexahydroazepino[4,5‐ b ]indole.