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Organocatalytic Asymmetric Arylative Dearomatization of 2,3‐Disubstituted Indoles Enabled by Tandem Reactions
Author(s) -
Zhang YuChen,
Zhao JiaJia,
Jiang Fei,
Sun SiBing,
Shi Feng
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201408551
Subject(s) - stereocenter , tandem , chemistry , enantioselective synthesis , cascade reaction , imine , quaternary carbon , alcohol , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , materials science , composite material
The organocatalytic asymmetric arylative dearomatization of indoles was achieved through two tandem approaches involving 2,3‐disubstituted indoles and quinone imine ketals. One approach utilized the enantioselective cascade 1,4 addition/alcohol elimination reaction, the other employed the one‐pot tandem arylative dearomatization/transfer hydrogenation sequence. In both cases, enantiomerically pure indole derivatives that bear an all‐carbon quaternary stereogenic center were generated in high yields and excellent stereoselectivities (all d.r.>95:5, up to 99 % ee ).