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Issue 33, 2014
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Stereoselective one-pot synthesis of β-alkylsulfide enol esters. Base-triggered rearrangement under mild conditions

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Abstract

A stereoselective one-pot procedure was developed to prepare S-substituted (Z)-enol esters through a base-triggered rearrangement. This transition metal-free multicomponent approach can be performed under an air atmosphere at room temperature, tolerates a wide set of chemical functionalities and generally affords high isolated yields. The (Z)-selectivity arises from the [1,4]-S- to O-acyl migration.

Graphical abstract: Stereoselective one-pot synthesis of β-alkylsulfide enol esters. Base-triggered rearrangement under mild conditions

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Publication details

The article was received on 15 May 2014, accepted on 02 Jul 2014 and first published on 02 Jul 2014


Article type: Paper
DOI: 10.1039/C4OB01011F
Citation: Org. Biomol. Chem., 2014,12, 6516-6526
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    Stereoselective one-pot synthesis of β-alkylsulfide enol esters. Base-triggered rearrangement under mild conditions

    A. A. Heredia, S. M. Soria-Castro, L. M. Bouchet, G. Oksdath-Mansilla, C. A. Barrionuevo, D. A. Caminos, F. R. Bisogno, J. E. Argüello and A. B. Peñéñory, Org. Biomol. Chem., 2014, 12, 6516
    DOI: 10.1039/C4OB01011F

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