Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/99384
Title: Study of substrate dependence on the chemoselectivity of the gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes
Authors: Huang, Chuhui
Kothandaraman, Prasath
Koh, Bing Qin
Chan, Philip Wai Hong
Keywords: DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds
Issue Date: 2012
Source: Huang, 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.
Series/Report no.: Organic & biomolecular chemistry
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.
URI: https://hdl.handle.net/10356/99384
http://hdl.handle.net/10220/17219
DOI: http://dx.doi.org/10.1039/c2ob26458g
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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