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

Beilstein J Org Chem

EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, United Kingdom.

Published: June 2020


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Article Abstract

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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7356285PMC
http://dx.doi.org/10.3762/bjoc.16.129DOI Listing

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