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Issue 45, 2012
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Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes

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Abstract

The effects of starting material substitution patterns on reaction selectivity for the gold(I)-catalysed cycloisomerisations of aryl substituted 1,7-enynes were investigated. The results indicated the chemoselectivity of the reaction to be highly substrate and catalyst dependent. Either the piperidine or the tetrahydro-1H-azepine product was obtained in moderate to excellent yields depending on the steric and/or electronic nature of the substrate and the gold(I) catalyst. Overall, six-membered nitrogen ring formation was found to be favoured in reactions with 1,7-enyne derivatives containing a disubstituted alkene moiety or not bearing a sterically bulky substituent or a gold(I) catalyst with a pendant sterically unencumbered phosphine ligand. Formation of the seven-membered nitrogen heterocycle was observed in reactions where the substrate contained a tetrasubstituted alkene unit or a sterically demanding substituent.

Graphical abstract: Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes

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Publication details

The article was received on 26 Jul 2012, accepted on 18 Sep 2012 and first published on 18 Sep 2012


Article type: Paper
DOI: 10.1039/C2OB26458G
Citation: Org. Biomol. Chem., 2012,10, 9067-9078
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    Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes

    C. Huang, P. Kothandaraman, B. Q. Koh and P. W. H. Chan, Org. Biomol. Chem., 2012, 10, 9067
    DOI: 10.1039/C2OB26458G

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