A general stereoselective method for the synthesis of cyclopropanecarboxylates. A new version of the homologous Horner–Wadsworth–Emmons reaction?

Organic & Biomolecular Chemistry Pub Date: 2007-11-28 DOI: 10.1039/B712145H

Abstract

The synthesis of α-, β- and γ-substituted α-phosphono-γ-lactones was accomplished using different ring closure and ring homologation strategies. It was found that the lactones could be selectively transformed into the corresponding ethyl cyclopropanecarboxylates by treatment with sodium ethoxide in boiling THF. The reported reaction provides an attractive alternative to the classical homologous Horner–Wadsworth–Emmons approach to the construction of cyclopropanes with electron-withdrawing functionalities.

Graphical abstract: A general stereoselective method for the synthesis of cyclopropanecarboxylates. A new version of the homologous Horner–Wadsworth–Emmons reaction
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