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

Autor: Alyn T. Davies, Mark D. Greenhalgh, Alexandra M. Z. Slawin, Andrew D. Smith
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 16, Iss 1, Pp 1572-1578 (2020)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.16.129
Popis: 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.
Databáze: Directory of Open Access Journals