Issue 11, 2021

α,β-Unsaturated acyl ammonium species as reactive intermediates in organocatalysis: an update

Abstract

α,β-Unsaturated acyl ammonium species are versatile intermediates that have been applied in a variety of transformations including Michael additions, domino reactions and cycloadditions. Many of these transformations are promoted by chiral Lewis base catalysts, enabling the rapid generation of molecular complexity with high stereochemical control. This review highlights recent developments in the generation and application of α,β-unsaturated acyl ammonium intermediates reported since a previous review of this area in 2016. Particular emphasis will be placed on reports providing mechanistic insight into catalytic transformations and observed selectivities. A perspective on current challenges and potential future developments in the field of α,β-unsaturated acyl ammonium catalysis is also provided.

Graphical abstract: α,β-Unsaturated acyl ammonium species as reactive intermediates in organocatalysis: an update

Article information

Article type
Review Article
Submitted
05 11月 2020
Accepted
12 12月 2020
First published
01 3月 2021
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2021,19, 2366-2384

α,β-Unsaturated acyl ammonium species as reactive intermediates in organocatalysis: an update

J. Bitai, M. T. Westwood and A. D. Smith, Org. Biomol. Chem., 2021, 19, 2366 DOI: 10.1039/D0OB02208J

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