dc.contributor.authorKothandaraman, Prasath
dc.contributor.authorKoh, Bing Qin
dc.contributor.authorLimpanuparb, Taweetham
dc.contributor.authorHirao, Hajime
dc.contributor.authorChan, Philip Wai Hong
dc.date.accessioned2013-10-18T02:28:15Z
dc.date.available2013-10-18T02:28:15Z
dc.date.copyright2013en_US
dc.date.issued2013
dc.identifier.citationKothandaraman, P., Koh, B. Q., Limpanuparb, T., Hirao, H.,& Chan, P. W. H. (2013). 1-(2′-Anilinyl)prop-2-yn-1-ol Rearrangement for Oxindole Synthesis. Chemistry - A European Journal, 19(6), 1978-1985.en_US
dc.identifier.issn0947-6539en_US
dc.identifier.urihttp://hdl.handle.net/10220/16575
dc.description.abstractA synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3- and 2-oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity.en_US
dc.language.isoenen_US
dc.relation.ispartofseriesChemistry - a European journalen_US
dc.title1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesisen_US
dc.typeJournal Article
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.identifier.doihttp://dx.doi.org/10.1002/chem.201202606


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