dc.contributor.authorHuang, Chuhui
dc.contributor.authorKothandaraman, Prasath
dc.contributor.authorKoh, Bing Qin
dc.contributor.authorChan, Philip Wai Hong
dc.date.accessioned2013-11-01T06:39:24Z
dc.date.available2013-11-01T06:39:24Z
dc.date.copyright2012en_US
dc.date.issued2012
dc.identifier.citationHuang, C., Kothandaraman, P., Koh, B. Q., & Chan, P. W. H. (2012). Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes. Organic & Biomolecular Chemistry, 10(45), 9067-9078.en_US
dc.identifier.urihttp://hdl.handle.net/10220/17219
dc.description.abstractThe 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.en_US
dc.language.isoenen_US
dc.relation.ispartofseriesOrganic & biomolecular chemistryen_US
dc.subjectDRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds
dc.titleStudy of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynesen_US
dc.typeJournal Article
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.identifier.doihttp://dx.doi.org/10.1039/c2ob26458g


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