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Chiral Ammonium Aryloxides: Efficient Multipurpose Basic Organocatalysts
Author(s) -
Godemert Jérémy,
Oudeyer Sylvain,
Levacher Vincent
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500616
Subject(s) - chemistry , aldol reaction , catalysis , organocatalysis , trifluoromethylation , protonation , enantioselective synthesis , michael reaction , intramolecular force , ammonium , tandem , lewis acids and bases , silylation , organic chemistry , combinatorial chemistry , medicinal chemistry , trifluoromethyl , ion , materials science , alkyl , composite material
This review summarizes the recent developments in chiral quaternary ammonium aryloxides as flexible organocatalysts that are able to act as both a Brønsted and Lewis base. A particular class of ammonium aryloxides, namely betaines, has emerged as an efficient class of catalysts. The performance of betaines stems mainly from the intramolecular nature of these ammonium ion pairs, leading to highly reactive catalytic species with a high level of organization. The above‐mentioned catalysts have been successfully applied to a wide range of asymmetric chemical transformations, including Mukaiyama aldol reactions, tandem Michael addition/lactonization sequences, trifluoromethylation reactions, aza‐Henry reactions, silyl enolates protonation reactions, and Steglich‐type rearrangements, with a high level of enantioselectivity.