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Issue 2, 2008
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A general stereoselective method for the synthesis of cyclopropanecarboxylates. A new version of the homologous Horner–Wadsworth–Emmons reaction

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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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Publication details

The article was received on 08 Aug 2007, accepted on 25 Oct 2007 and first published on 28 Nov 2007


Article type: Paper
DOI: 10.1039/B712145H
Org. Biomol. Chem., 2008,6, 308-318

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

    H. Krawczyk, K. Wąsek, J. Kędzia, J. Wojciechowski and W. M. Wolf, Org. Biomol. Chem., 2008, 6, 308
    DOI: 10.1039/B712145H

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