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Synlett 1994; 1994(9): 729-731
DOI: 10.1055/s-1994-22988
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A Short Access to α-Fluoro-β,γ-Unsaturated Esters

Olivier Piva*
  • *Laboratoire des Réarrangements Thermiques et Photochimiques, associé au CNRS, Université de Reims - Champagne - Ardenne , UFR Sciences BP 347 - 51062 Reims cedex - France.
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Publication Date:
18 September 2002 (online)

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α-Fluoro-β,γ-unsaturated esters are synthetized in high yields by photodeconjugation of the α-fluoro-α,β-unsaturated isomers in the presence of a base. In contrast to the α-bromo analogues, no homolytic cleavage of the carbon-halogen bond is observed during the irradiation. The reaction has been successfully applied to the enantioselective synthesis of optically active fluoroesters when conducted with a chiral protonating agent.

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