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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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
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author Davies, Alyn T
Greenhalgh, Mark D
Slawin, Alexandra M Z
Smith, Andrew D
author_facet Davies, Alyn T
Greenhalgh, Mark D
Slawin, Alexandra M Z
Smith, Andrew D
author_sort Davies, Alyn T
collection PubMed
description 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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spelling pubmed-73562852020-07-22 NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides Davies, Alyn T Greenhalgh, Mark D Slawin, Alexandra M Z Smith, Andrew D Beilstein J Org Chem Letter 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. Beilstein-Institut 2020-06-30 /pmc/articles/PMC7356285/ /pubmed/32704323 http://dx.doi.org/10.3762/bjoc.16.129 Text en Copyright © 2020, Davies et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Davies, Alyn T
Greenhalgh, Mark D
Slawin, Alexandra M Z
Smith, Andrew D
NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
title NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
title_full NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
title_fullStr NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
title_full_unstemmed NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
title_short NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
title_sort nhc-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
topic Letter
url 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
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