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Issue 2, 2016
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Triazole–gold promoted intermolecular propargyl alcohol addition to alkyne: the reaction cascade toward substituted allenes

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Abstract

Gold-catalyzed intermolecular propargyl alcohol addition to alkyne was achieved. The reaction of propargyl alcohol with a typical gold catalyst gave the hydration product almost exclusively. The triazole gold catalyst (TA–Au) successfully prevented the hydration, giving the vinyl ether followed by a 3,3-rearrangement. Synthetically useful substituted allenes were formed with high efficiency, substrate tolerability and chemoselectivity. Also, more than 95% chirality transfer from propargyl alcohol to allene was obtained.

Graphical abstract: Triazole–gold promoted intermolecular propargyl alcohol addition to alkyne: the reaction cascade toward substituted allenes

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Publication details

The article was received on 02 Oct 2015, accepted on 20 Oct 2015 and first published on 21 Oct 2015


Article type: Communication
DOI: 10.1039/C5CC08233A
Author version available: Download Author version (PDF)
Citation: Chem. Commun., 2016,52, 296-299
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    Triazole–gold promoted intermolecular propargyl alcohol addition to alkyne: the reaction cascade toward substituted allenes

    S. Hosseyni, S. Ding, Y. Su, N. G. Akhmedov and X. Shi, Chem. Commun., 2016, 52, 296
    DOI: 10.1039/C5CC08233A

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