Pathway for the stereocontrolled Z and E production of α,α- difluorine-substituted phenyl butenoates

Wadih Ghattas, Corinna R. Hess, Gilles Iacazio, Renaud Hardré, Judith P. Klinman, Marius Réglier

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

An efficient preparation of pure ethyl Z- and E-α,α-difluoro-4- phenyl-3-butenoate 1a and 1b together with the corresponding acids 2a and 2b is described. The procedures involve stereocontrolled additions of CF2CO2Et to phenylacetylene or β-bromostyrene. Compound 1a is easily obtained by addition of CF2CO2Et to phenylacetylene via a mechanism where the stereochemistry is controlled by an electron-transfer process to produce predominantly the Z vinyl anion. The product 1b is obtained by CF2CO2Et addition-elimination to Z- or E-β-bromostyrenes via a mechanism where the stereochemistry is controlled by steric factors in the conformational equilibration of the intermediates.

Original languageEnglish
Pages (from-to)8618-8621
Number of pages4
JournalJournal of Organic Chemistry
Volume71
Issue number22
DOIs
StatePublished - 27 Oct 2006
Externally publishedYes

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