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Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho ‐Quinone Methides with 2‐Indolylmethanols
Author(s) -
Sun Meng,
Ma Chun,
Zhou SiJia,
Lou SaiFan,
Xiao Jian,
Jiao Yinchun,
Shi Feng
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.201901955
Subject(s) - catalysis , quinone , in situ , quinone methide , chemistry , enantioselective synthesis , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry
The first catalytic asymmetric (4+3) cyclization of in situ generated ortho ‐quinone methides with 2‐indolylmethanols has been established, which constructed seven‐membered heterocycles in high yields (up to 95 %) and excellent enantioselectivity (up to 98 %). This approach not only represents the first catalytic asymmetric (4+3) cyclization of o ‐hydroxybenzyl alcohols, but also enabled an unprecedented catalytic asymmetric (4+3) cyclization of 2‐indolylmethanols. In addition, a scarcely reported catalytic asymmetric (4+3) cyclization of para ‐quinone methide derivatives was accomplished.