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Issue 14, 2021

NHC-catalyzed covalent activation of heteroatoms for enantioselective reactions

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Abstract

Covalent activation of heteroatoms enabled by N-heterocyclic carbene (NHC) organic catalysts for enantioselective reactions is evaluated and summarized in this review. To date, sulfur, oxygen, and nitrogen atoms can be activated in this manner to react with another substrate to construct chiral carbon–heteroatom bonds with high optical enantioselectivities. The activation starts with addition of an NHC catalyst to the carbonyl moiety (aldehyde or imine) of substrates that contain heteroatoms. The key in this approach is the formation of intermediates covalently bound to the NHC catalyst, in which the heteroatom of the substrate is activated as a nucleophilic reactive site.

Graphical abstract: NHC-catalyzed covalent activation of heteroatoms for enantioselective reactions

Article information


Submitted
25 Jan 2021
Accepted
16 Feb 2021
First published
02 Mar 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021,12, 5037-5043
Article type
Review Article

NHC-catalyzed covalent activation of heteroatoms for enantioselective reactions

R. Song, Z. Jin and Y. R. Chi, Chem. Sci., 2021, 12, 5037 DOI: 10.1039/D1SC00469G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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