Stereoselective Synthesis of α-Fluoro-β-Trifluromethyl-α-β- Unsaturated Esters by Horner-Wadsworth-Emmons Coupling

Shainaz M. Landge; Béla Tö Rök

doi:10.2174/1570178611666140124001052

Stereoselective Synthesis of α-Fluoro-β-Trifluromethyl-α-β- Unsaturated Esters by Horner-Wadsworth-Emmons Coupling

Shainaz M. Landge
, Béla Tö Rök

Biochemistry, Chemistry & Physics

University of Massachusetts Boston

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

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.

Original language	American English
Journal	Letters in Organic Chemistry
Volume	11
DOIs	https://doi.org/10.2174/1570178611666140124001052
State	Published - Jan 1 2013

Disciplines

Chemistry

Keywords

Stereoselective Synthesis

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http://dx.doi.org/10.2174/1570178611666140124001052

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title = "Stereoselective Synthesis of α-Fluoro-β-Trifluromethyl-α-β- Unsaturated Esters by Horner-Wadsworth-Emmons Coupling",

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.",

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language = "American English",

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T1 - Stereoselective Synthesis of α-Fluoro-β-Trifluromethyl-α-β- Unsaturated Esters by Horner-Wadsworth-Emmons Coupling

AU - Landge, Shainaz M.

AU - Rök, Béla Tö

PY - 2013/1/1

Y1 - 2013/1/1

N2 - 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.

AB - 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.

KW - Stereoselective Synthesis

UR - https://digitalcommons.georgiasouthern.edu/chem-facpubs/58

UR - http://dx.doi.org/10.2174/1570178611666140124001052

U2 - 10.2174/1570178611666140124001052

DO - 10.2174/1570178611666140124001052

M3 - Article

SN - 1570-1786

VL - 11

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

ER -

Stereoselective Synthesis of α-Fluoro-β-Trifluromethyl-α-β- Unsaturated Esters by Horner-Wadsworth-Emmons Coupling

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