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Design and Catalytic Asymmetric Construction of Axially Chiral 3,3′‐Bisindole Skeletons
Author(s) -
Ma Chun,
Jiang Fei,
Sheng FengTao,
Jiao Yinchun,
Mei GuangJian,
Shi Feng
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201811177
Subject(s) - enantioselective synthesis , axial chirality , axial symmetry , chirality (physics) , catalysis , yield (engineering) , chemistry , stereochemistry , materials science , combinatorial chemistry , organic chemistry , physics , mathematics , composite material , geometry , chiral symmetry , quantum mechanics , quark , nambu–jona lasinio model
The first catalytic asymmetric construction of 3,3′‐bisindole skeletons bearing both axial and central chirality has been established by organocatalytic asymmetric addition reactions of 2‐substituted 3,3′‐bisindoles with 3‐indolylmethanols (up to 98 % yield, all >95:5 d.r., >99 % ee ). This reaction also represents the first highly enantioselective construction of axially chiral 3,3′‐bisindole skeletons, and utilizes the strategy of introducing a bulky group to the ortho ‐position of prochiral 3,3′‐bisindoles. This reaction not only provides a good example for simultaneously controlling axial and central chirality in one operation, but also serves as a new strategy for catalytic enantioselective construction of axially chiral 3,3′‐bisindole backbones from prochiral substrates.