Issue 49, 2016

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

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

Supplementary files

Article information

Article type
Communication
Submitted
11 Apr 2016
Accepted
16 May 2016
First published
16 May 2016

Chem. Commun., 2016,52, 7687-7690

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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