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Journal Articles ChemCatChem Year : 2016

Chiral Ammonium Aryloxides: Efficient Multipurpose Basic Organocatalysts

Abstract

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.

Dates and versions

hal-02046209 , version 1 (22-02-2019)

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Jérémy Godemert, Sylvain Oudeyer, Vincent Levacher. Chiral Ammonium Aryloxides: Efficient Multipurpose Basic Organocatalysts. ChemCatChem, 2016, 8 (1), pp.74-85. ⟨10.1002/cctc.201500616⟩. ⟨hal-02046209⟩
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