NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides

The N-heterocyclic carbene (NHC)-catalyzed formal [2 + 2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring opening with an amine or a reducing agent is described. The resulting β-trifluoromethyl-β-hydroxyamide and alcohol products are produced with reasonable di...

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Detalles Bibliográficos
Autores principales: Davies, Alyn T, Greenhalgh, Mark D, Slawin, Alexandra M Z, Smith, Andrew D
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7356285/
https://www.ncbi.nlm.nih.gov/pubmed/32704323
http://dx.doi.org/10.3762/bjoc.16.129
Descripción
Sumario:The N-heterocyclic carbene (NHC)-catalyzed formal [2 + 2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring opening with an amine or a reducing agent is described. The resulting β-trifluoromethyl-β-hydroxyamide and alcohol products are produced with reasonable diastereocontrol (typically ≈70:30 dr) and excellent enantioselectivity, and they can be isolated in moderate to good yield as a single diastereoisomer.

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