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

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.

SUBMITTER: Davies AT 

PROVIDER: S-EPMC7356285 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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

Davies Alyn T AT   Greenhalgh Mark D MD   Slawin Alexandra M Z AMZ   Smith Andrew D AD  

Beilstein journal of organic chemistry 20200630

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. ...[more]