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Issue 37, 2012
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Direct allenol-based stereocontrolled access to substituted (E)-1,3-enynes

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Abstract

A stereoselective synthesis of 1-substituted (E)-2-aryl-but-1-en-3-ynes, including tetrasubstituted alkenes, has been developed from aryl-substituted α-allenols by treatment with the AcCl–NaOH (aqueous) system. This transformation might be explained through the elimination of acetic acid, made up of a δ-hydrogen and the acetate group in the initially formed α-allenic acetate.

Graphical abstract: Direct allenol-based stereocontrolled access to substituted (E)-1,3-enynes

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Publication details

The article was received on 05 Jun 2012, accepted on 03 Aug 2012 and first published on 03 Aug 2012


Article type: Paper
DOI: 10.1039/C2OB26085A
Citation: Org. Biomol. Chem., 2012,10, 7603-7609
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    Direct allenol-based stereocontrolled access to substituted (E)-1,3-enynes

    B. Alcaide, P. Almendros and T. Martínez del Campo, Org. Biomol. Chem., 2012, 10, 7603
    DOI: 10.1039/C2OB26085A

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