Stereoselective Synthesis of α-fluoro-β-trifluoromethyl-α,β-unsaturated Esters by Horner-Wadsworth-Emmons Coupling
Shainaz M. Landge and Bela Torok
Affiliation: Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Blvd., Boston, MA, USA.
α-Fluoro-β-trifluoromethyl-α,β-unsaturated esters were synthesized via the reaction of diethyl (1-fluoro-1-
carbethoxymethyl) phosphonate with a variety of aromatic/heterocyclic trifluoromethyl ketones and trifluoroacetaldehyde
ethyl hemiacetal by the Horner-Wadsworth-Emmons (HWE) coupling. The effect of base, solvent, as well as reactant ratio
has been investigated. The present method is highly stereoselective, attractive and convenient for the synthesis of the
target compounds due to the availability of the reagents, simplicity of the approach and good yields of the products.
Keywords: α-fluoro-β-trifluoromethyl-α-β-unsaturated esters, Horner-Wadsworth-Emmons coupling, trifluoromethyl ketones.
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