Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated  ortho ‐Quinone Methides with 2‐Indolylmethanols | Zendy

Sun Meng | Zendy; Ma Chun | Zendy; Zhou SiJia | Zendy; Lou SaiFan | Zendy; Xiao Jian | Zendy; Jiao Yinchun | Zendy; Shi Feng | Zendy

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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 , quinone methide , in situ , chemistry , enantioselective synthesis , combinatorial 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.

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