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Issue 49, 2016
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Ligand-controlled gold-catalyzed cycloisomerization of 1,n-enyne esters toward synthesis of dihydronaphthalene

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Abstract

We describe herein a gold-catalyzed rearrangement of propargyl esters followed by allene–ene cyclization to afford substituted bicyclic [4.4.0] dihydronaphthalene compounds. This method is also applied to vinylethers and vinylamines of 1,7-enyne esters to form dihydroquinoline and dihydrobenzopyran structures. The basis of this transformation is the ligand-controlled preferential activation of the alkene over the allene, affording the desired aromatic bicyclic structures in moderate to excellent yields.

Graphical abstract: Ligand-controlled gold-catalyzed cycloisomerization of 1,n-enyne esters toward synthesis of dihydronaphthalene

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Publication details

The article was received on 11 Apr 2016, accepted on 16 May 2016 and first published on 16 May 2016


Article type: Communication
DOI: 10.1039/C6CC03032G
Citation: Chem. Commun., 2016,52, 7687-7690
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    Ligand-controlled gold-catalyzed cycloisomerization of 1,n-enyne esters toward synthesis of dihydronaphthalene

    S. K. Thummanapelli, S. Hosseyni, Y. Su, N. G. Akhmedov and X. Shi, Chem. Commun., 2016, 52, 7687
    DOI: 10.1039/C6CC03032G

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