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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.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 .
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.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.relation.ispartofTetrahedron: Asymmetryen
dc.rights© 2017 The Authors. This is an open access article under the CC BY license (
dc.subjectQD Chemistryen
dc.titleEnantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridinesen
dc.typeJournal articleen
dc.contributor.sponsorThe Royal Societyen
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.description.statusPeer revieweden

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