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Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

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dc.contributor.authorCampbell, Craig Donald
dc.contributor.authorJoannesse, Caroline
dc.contributor.authorMorrill, Louis Christian
dc.contributor.authorPhilpa, Douglas
dc.contributor.authorSmith, Andrew David
dc.date.accessioned2015-06-03T09:10:03Z
dc.date.available2015-06-03T09:10:03Z
dc.date.issued2015-03-14
dc.identifier.citationCampbell , C D , Joannesse , C , Morrill , L C , Philpa , D & Smith , A D 2015 , ' Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates ' , Organic & Biomolecular Chemistry , vol. 13 , no. 10 , pp. 2895-2900 . https://doi.org/10.1039/C4OB02629Ben
dc.identifier.issn1477-0520
dc.identifier.otherPURE: 167952761
dc.identifier.otherPURE UUID: 934caf80-2edc-45de-bc63-4c4ee2ab8713
dc.identifier.otherWOS: 000350674400009
dc.identifier.otherPubMed: 25646598
dc.identifier.otherScopus: 84923872943
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567500
dc.identifier.urihttps://hdl.handle.net/10023/6733
dc.descriptionThe authors would like to thank the Royal Society for a University Research Fellowship (ADS), The Carnegie Trust for the Universities of Scotland (CDC and LCM) and the EPSRC (CJ) for funding, and the EPSRC National Mass Spectrometry Service Centre (Swansea).en
dc.description.abstractTriazolinylidenes promote γ-selective C-carboxylation (up to 99 : 1 regioselectivity) in the O- to C-carboxyl transfer of furanyl carbonates in contrast to DMAP that promotes preferential α-C-carboxylation with moderate regiocontrol (typically 60 : 40 regioselectivity). The generality of this process is described and a simple mechanistic and kinetic model postulated to account for the observed regioselectivity
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.rightsCopyright 2015 the Authors. This open access article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).en
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleRegiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonatesen
dc.typeJournal articleen
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/C4OB02629B
dc.description.statusPeer revieweden
dc.identifier.urlhttp://www.rsc.org/suppdata/ob/c4/c4ob02629b/c4ob02629b1.pdfen
dc.identifier.urlhttp://www.rsc.org/suppdata/ob/c4/c4ob02629b/c4ob02629b2.xmlen


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