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

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 molec...

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Veröffentlicht in:Organic & biomolecular chemistry 2021-03, Vol.19 (11), p.2366-2384
Hauptverfasser: Bitai, Jacqueline, Westwood, Matthew T, Smith, Andrew D
Format: Artikel
Sprache:eng
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Zusammenfassung: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. 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob02208j