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Organocatalytic Enantioselective Synthesis of Chiral Allenes: Remote Asymmetric 1,8‐Addition of Indole Imine Methides
Author(s) -
Li Xingguang,
Sun Jianwei
Publication year - 2020
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.202006137
Subject(s) - enantioselective synthesis , chemistry , imine , bifunctional , indole test , nucleophile , organocatalysis , phosphoric acid , organic chemistry , combinatorial chemistry , catalysis
An organocatalytic enantioconvergent synthesis of chiral tetrasubstituted allenes is disclosed. With suitable chiral phosphoric acid catalysts, a range of racemic indole‐substituted propargylic alcohols reacted with nucleophiles to provide efficient access to a series of enantioenriched allenes with high enantioselectivities. Control experiments suggested a mechanism involving remotely controlled asymmetric 1,8‐addition of the in situ generated indole imine methide via a bifunctional transition state.