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Catalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates : synthetic and computational studies

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dc.contributor.authorGould, Eoin
dc.contributor.authorWalden, Daniel M.
dc.contributor.authorKasten, Kevin
dc.contributor.authorJohnston, Ryne C.
dc.contributor.authorWu, Jiufeng
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorMustard, Thomas J. L.
dc.contributor.authorJohnston, Brittany
dc.contributor.authorDavies, Tony
dc.contributor.authorHa-Yeon Cheong, Paul
dc.contributor.authorSmith, Andrew D.
dc.date.accessioned2014-08-18T10:31:03Z
dc.date.available2014-08-18T10:31:03Z
dc.date.issued2014-07-03
dc.identifier.citationGould , E , Walden , D M , Kasten , K , Johnston , R C , Wu , J , Slawin , A M Z , Mustard , T J L , Johnston , B , Davies , T , Ha-Yeon Cheong , P & Smith , A D 2014 , ' Catalyst selective and regiodivergent O- to C- or N- carboxyl transfer of pyrazolyl carbonates : synthetic and computational studies ' , Chemical Science , vol. 5 , no. 9 , pp. 3651-3658 . https://doi.org/10.1039/C4SC00879Ken
dc.identifier.issn2041-6520
dc.identifier.otherPURE: 141290396
dc.identifier.otherPURE UUID: b86f4817-91d8-4894-8692-32f912058a57
dc.identifier.otherRIS: urn:DF36793752F4448F5BFAAB34BAD3371D
dc.identifier.otherScopus: 84962463383
dc.identifier.otherORCID: /0000-0002-2104-7313/work/36567509
dc.identifier.otherORCID: /0000-0002-8987-5561/work/27750842
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56862088
dc.identifier.otherWOS: 000340695800040
dc.identifier.urihttps://hdl.handle.net/10023/5182
dc.descriptionThe authors acknowledge the Royal Society for a University Research Fellowship (ADS) and the EPSRC and Merck Sharp & Dohme Ltd (CASE award to EG) for funding, and the EPSRC National Mass Spectrometry Service Centre (Swansea). The research leading to these results has received funding from the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) / ERC grant agreement n° 279850.en
dc.description.abstractThe regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates is described, with DMAP giving preferential N-carboxylation and triazolinylidenes promoting selective C-carboxylation (both with up to >99 : 1 regioselectivity). An enantioselective O- to C-carboxyl variant using NHC catalysis is demonstrated (up to 92% ee), while mechanistic and DFT studies outline the pathways operative in this system and provide insight into the reasons for the observed selectivity.
dc.format.extent8
dc.language.isoeng
dc.relation.ispartofChemical Scienceen
dc.rights© Royal Society of Chemistry 2014. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).en
dc.subjectQD Chemistryen
dc.subject.lccQDen
dc.titleCatalyst selective and regiodivergent O- to C- or N-carboxyl transfer of pyrazolyl carbonates : synthetic and computational studiesen
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/10.1039/C4SC00879K
dc.description.statusPeer revieweden
dc.identifier.urlhttp://www.rsc.org/suppdata/sc/c4/c4sc00879k/c4sc00879k1.pdfen
dc.identifier.urlhttp://www.rsc.org/suppdata/sc/c4/c4sc00879k/c4sc00879k2.cifen


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