Letters in Organic Chemistry

Gwilherm Evano
Free University of Brussels
Brussels
Belgium

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Stereoselective Synthesis of α-fluoro-β-trifluoromethyl-α,β-unsaturated Esters by Horner-Wadsworth-Emmons Coupling

Author(s): Shainaz M. Landge, Bela Torok.

Abstract:

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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Article Details

VOLUME: 11
ISSUE: 5
Year: 2014
Page: [374 - 379]
Pages: 6
DOI: 10.2174/1570178611666140124001052
Price: $58