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

Autor: Bitai J; EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, Fife, Scotland, KY16 9ST, UK. ads10@st-andrews.ac.uk., Westwood MT, Smith AD
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2021 Mar 21; Vol. 19 (11), pp. 2366-2384. Date of Electronic Publication: 2021 Mar 02.
DOI: 10.1039/d0ob02208j
Abstrakt: 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.
Databáze: MEDLINE