Direct Access to β-Trifluoromethyl-β-hydroxy Thioesters by Biomimetic Organocatalytic Enantioselective Aldol Reaction
Jin Hyun Park1, Jae Hun Sim1, Choong Eui Song1
1Department of Chemistry , Sungkyunkwan University , Suwon 16419 , Korea.
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.
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