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dc.contributor.authorKerr, Ryan W. F.
dc.contributor.authorGreenhalgh, Mark D.
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorArnold, Polly L.
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2017-01-13T10:30:13Z
dc.date.available2017-01-13T10:30:13Z
dc.date.issued2017-01-15
dc.identifier.citationKerr , R W F , Greenhalgh , M D , Slawin , A M Z , Arnold , P L & Smith , A D 2017 , ' Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines ' , Tetrahedron: Asymmetry , vol. 28 , no. 1 , pp. 125-134 . https://doi.org/10.1016/j.tetasy.2016.10.012en
dc.identifier.issn0957-4166
dc.identifier.otherPURE: 247180829
dc.identifier.otherPURE UUID: 3fe8c26e-cde5-4660-98a9-7e7ff8223a23
dc.identifier.otherScopus: 85007006414
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567480
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861734
dc.identifier.otherWOS: 000392771200015
dc.identifier.urihttp://hdl.handle.net/10023/10090
dc.descriptionWe thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1) (R.W.F.K.) for funding. The European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC Grant Agreement No. 279850 is also acknowledged. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractAn enantioselective N-heterocyclic carbene catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and α-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of a model to explain these observations.
dc.language.isoeng
dc.relation.ispartofTetrahedron: Asymmetryen
dc.rights© 2017 The Authors. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).en
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleEnantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridinesen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.Biomedical Sciences Research Complexen
dc.identifier.doihttps://doi.org/10.1016/j.tetasy.2016.10.012
dc.description.statusPeer revieweden


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