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dc.contributor.authorHodgson, David M.en_GB
dc.contributor.authorGlen, Rebeccaen_GB
dc.contributor.authorGrant, Guy H.en_GB
dc.contributor.authorRedgrave, Alison J.en_GB
dc.date.accessioned2013-09-23T12:33:24Z
dc.date.available2013-09-23T12:33:24Z
dc.date.issued2003
dc.identifier.citationHodgson, D.M., Glen, R., Grant, G.H. and Redgrave, A.J. (2003) 'Catalytic Enantioselective [3 + 2]-Cycloadditions of Diazoketone-Derived Aryl-Substituted Carbonyl Ylides', The Journal of Organic Chemistry, 68(2), pp.581-586en_GB
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.doi10.1021/jo026307t
dc.identifier.urihttp://hdl.handle.net/10547/302107
dc.description.abstractAn evaluation of α-aryl-α-diazodiones in tandem carbonyl ylide formation−enantioselective [3 + 2]-cycloaddition reactions is described. Such substrates were designed to allow investigation of the electronic characteristics of the dipole upon asymmetric induction. Intramolecular cycloadditions (with a tethered alkene dipolarophile) were found to occur in good to quantitative yields, with a difference in ee exhibited by the two electronically different diazodiones 8 and 9. Intermolecular cycloadditions using diazodiones 12 and 13 with DMAD and arylacetylenes 16−18 again demonstrated that electronics play a key role in determining the outcome of the cycloaddition reactions. Enantioselectivities of up to 76% were observed.
dc.language.isoenen
dc.publisherAmerican Chemical Societyen_GB
dc.relation.urlhttp://pubs.acs.org/doi/abs/10.1021/jo026307ten_GB
dc.rightsArchived with thanks to The Journal of Organic Chemistryen_GB
dc.titleCatalytic enantioselective [3 + 2]-cycloadditions of diazoketone-derived aryl-substituted carbonyl ylidesen
dc.typeArticleen
dc.contributor.departmentUniversity of Oxforden_GB
dc.contributor.departmentGlaxoSmithKline Medicines Research Centreen_GB
dc.identifier.journalThe Journal of Organic Chemistryen_GB
html.description.abstractAn evaluation of α-aryl-α-diazodiones in tandem carbonyl ylide formation−enantioselective [3 + 2]-cycloaddition reactions is described. Such substrates were designed to allow investigation of the electronic characteristics of the dipole upon asymmetric induction. Intramolecular cycloadditions (with a tethered alkene dipolarophile) were found to occur in good to quantitative yields, with a difference in ee exhibited by the two electronically different diazodiones 8 and 9. Intermolecular cycloadditions using diazodiones 12 and 13 with DMAD and arylacetylenes 16−18 again demonstrated that electronics play a key role in determining the outcome of the cycloaddition reactions. Enantioselectivities of up to 76% were observed.


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