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Direct Access to β-Trifluoromethyl-β-hydroxy Thioesters by Biomimetic Organocatalytic Enantioselective Aldol Reaction

Author:
Park, Jin Hyun, Sim, Jae Hun, Song, Choong Eui
Source:
Organic letters 2019 v.21 no.12 pp. 4567-4570
ISSN:
1523-7052
Subject:
biomimetics, catalysts, catalytic activity, chemical reactions, enantioselectivity, ketones, malonic acid, moieties, pharmacology, polyketides, thioesters
Abstract:
A broadly applicable biomimetic enantioselective decarboxylative catalytic aldol reaction of trifluoromethyl ketones with malonic acid half-thioesters (MAHTs) is described. Utilizing cinchona-based thioureas as highly efficient polyketide synthase-mimic catalysts, chiral tertiary aldols, β-trifluoromethyl-β-hydroxy thioesters, were obtained in up to 99% yield and 95% ee. Facile transformation of the thioester moiety of the aldol adducts showcases the synthetic utility of this biomimetic aldol protocol to deliver a range of chiral trifluoromethylated tertiary aldol pharmacophores.
Agid:
6478173