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N- to C-sulfonyl photoisomerisation of dihydropyridinones : a synthetic and mechanistic study

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dc.contributor.authorYeh, Pei-Pei
dc.contributor.authorTaylor, James Edward
dc.contributor.authorStark, Daniel Graham
dc.contributor.authorDaniels, David Sydney Bernard
dc.contributor.authorFallan, Charlene
dc.contributor.authorWalton, John Christopher
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2017-10-17T16:30:29Z
dc.date.available2017-10-17T16:30:29Z
dc.date.issued2017-10-16
dc.identifier.citationYeh , P-P , Taylor , J E , Stark , D G , Daniels , D S B , Fallan , C , Walton , J C & Smith , A D 2017 , ' N- to C-sulfonyl photoisomerisation of dihydropyridinones : a synthetic and mechanistic study ' , Organic & Biomolecular Chemistry , vol. 15 , no. 42 , pp. 8914-8922 . https://doi.org/10.1039/C7OB01699Aen
dc.identifier.issn1477-0520
dc.identifier.otherPURE: 250686496
dc.identifier.otherPURE UUID: daca5ef1-7726-428a-864d-578d85a47c6f
dc.identifier.otherScopus: 85032728191
dc.identifier.otherORCID: /0000-0002-2104-7313/work/37898070
dc.identifier.otherORCID: /0000-0003-2746-6276/work/56638735
dc.identifier.otherWOS: 000414242100009
dc.identifier.urihttps://hdl.handle.net/10023/11872
dc.descriptionThe authors thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013) ERC Grant Agreement no. 279850 (CF and JET) and EPSRC grant number EP/J018139/1 (DSBD) for funding. ADS thanks the Royal Society for a Wolfson Research Merit Award.en
dc.description.abstractThe scope and limitations of a photoinitiated N- to C-sulfonyl migration process within a range of dihydropyridinones is assessed. This sulfonyl transfer proceeds without erosion of either diastereo- or enantiocontrol, and is general across a range of N-sulfonyl substituents (SO2R; R = Ph, 4-MeC6H4, 4-MeOC6H4, 4-NO2C6H4, Me, Et) as well as C(3)-(aryl, heteroaryl, alkyl and alkenyl) and C(4)-(aryl and ester) substitution. Crossover reactions indicate an intermolecular step is operative within the formal migration process, although no crossover from C-sulfonyl products was observed. EPR studies indicate the intermediacy of a sulfonyl radical and a mechanism is proposed based upon these observations.
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.rightsCopyright 2017 the authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licenceen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleN- to C-sulfonyl photoisomerisation of dihydropyridinones : a synthetic and mechanistic studyen
dc.typeJournal articleen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEuropean Commissionen
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/10.1039/C7OB01699A
dc.description.statusPeer revieweden
dc.identifier.urlhttp://www.rsc.org/suppdata/c7/ob/c7ob01699a/c7ob01699a1.pdfen
dc.identifier.grantnumberEP/J018139/1en
dc.identifier.grantnumberN/Aen
dc.identifier.grantnumberEP/J018139/1en


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