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Axially Chiral Aryl‐Alkene‐Indole Framework: A Nascent Member of the Atropisomeric Family and Its Catalytic Asymmetric Construction
Author(s) -
Wang CongShuai,
Li TianZhen,
Liu SiJia,
Zhang YuChen,
Deng Shuang,
Jiao Yinchun,
Shi Feng
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000131
Subject(s) - alkene , chemistry , enantioselective synthesis , aryl , indole test , axial symmetry , axial chirality , combinatorial chemistry , chirality (physics) , catalysis , stereochemistry , organic chemistry , physics , chiral symmetry breaking , alkyl , nambu–jona lasinio model , quantum mechanics , quark
Summary of main observation and conclusion A new class of axially chiral aryl‐alkene‐indole frameworks have been designed, and the first catalytic asymmetric construction of such scaffolds has been established by the strategy of organocatalytic ( Z / E )‐selective and enantioselective (4+3) cyclization of 3‐alkynyl‐2‐indolylmethanols with 2‐naphthols or phenols (all >95 : 5 E / Z , up to 98% yield, 97% ee). This reaction also represents the first catalytic asymmetric construction of axially chiral alkene‐heteroaryl scaffolds, which will add a new member to the atropisomeric family. This approach has not only confronted the great challenges in constructing axially chiral alkene‐heteroaryl scaffolds but also provided a powerful strategy for the enantioselective construction of axially chiral aryl‐alkene‐indole frameworks.