TY - JOUR A1 - Davies, Alyn T. A1 - Greenhalgh, Mark D. A1 - Slawin, Alexandra M. Z. A1 - Smith, Andrew D. T1 - NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides JF - Beilstein Journal of Organic Chemistry PY - 2020/// VL - 16 SP - 1572 EP - 1578 SN - 1860-5397 DO - 10.3762/bjoc.16.129 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.16.129 KW - enantioselective catalysis KW - formal [2 + 2] cycloaddition KW - N-heterocyclic carbene KW - ring opening KW - trifluoromethyl group N2 - 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. ER -