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Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines

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dc.contributor.authorSmith, Siobhan Rose
dc.contributor.authorFallan, Charlene
dc.contributor.authorTaylor, James Edward
dc.contributor.authorMcLennan, Ross Sinclair
dc.contributor.authorDaniels, David Sydney Bernard
dc.contributor.authorMorrill, Louis Christian
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2015-07-24T10:10:01Z
dc.date.available2015-07-24T10:10:01Z
dc.date.issued2015-07-13
dc.identifier.citationSmith , S R , Fallan , C , Taylor , J E , McLennan , R S , Daniels , D S B , Morrill , L C , Slawin , A M Z & Smith , A D 2015 , ' Asymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridines ' , Chemistry - A European Journal , vol. 21 , no. 29 , pp. 10530–10536 . https://doi.org/10.1002/chem.201501271en
dc.identifier.issn0947-6539
dc.identifier.otherPURE: 184426478
dc.identifier.otherPURE UUID: bc5a8d9a-5cdb-49b7-b005-15f0fe83f974
dc.identifier.otherScopus: 84934299973
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567498
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861552
dc.identifier.otherWOS: 000357328200036
dc.identifier.urihttps://hdl.handle.net/10023/7021
dc.descriptionThe authors thank the Royal Society for a University Research Fellowship (A.D.S.) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007—2013), ERC Grant Agreement No. 279850 (C.F. and J.E.T.), GSK (CASE award to S.R.S.) and EPSRC grant No. EP/J018139/1 (D.S.B.D.) for funding.en
dc.description.abstractA highly enantioselective Lewis base-catalysed formal [3+2] cycloaddition of ammonium enolates and oxaziridines to give stereodefined oxazolidin-4-ones in high yield is described. Employing an enantioenriched oxaziridine in this process leads to a matched/mis-matched effect with the isothiourea catalyst and allowed the synthesis of either syn- or anti-stereodefined oxazolidin-4-ones in high dr, yield and ee. Additionally, the oxazolidin-4-one products have been derivatised to afford functionalised enantioenriched building blocks.
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.rights© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en
dc.subjectOrganocatalysisen
dc.subjectNitrogen heterocyclesen
dc.subjectOxygen heterocyclesen
dc.subjectAsymmetric synthesisen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleAsymmetric isothiourea-catalysed formal [3+2] cycloadditions of ammonium enolates with oxaziridinesen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1002/chem.201501271
dc.description.statusPeer revieweden
dc.identifier.urlhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201501271/suppinfoen
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberEP/K031252/1en
dc.identifier.grantnumberEP/K039210/1en


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