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dc.contributor.authorCain, David L.
dc.contributor.authorMcLaughlin, Calum
dc.contributor.authorMolloy, John
dc.contributor.authorCarpenter-Warren, Cameron
dc.contributor.authorAnderson, Niall A.
dc.contributor.authorWatson, Allan J. B.
dc.date.accessioned2019-10-23T23:36:49Z
dc.date.available2019-10-23T23:36:49Z
dc.date.issued2019-04
dc.identifier256116346
dc.identifiereb1d9ceb-4a87-41ca-b663-02cccd055084
dc.identifier85064268333
dc.identifier000466807700006
dc.identifier.citationCain , D L , McLaughlin , C , Molloy , J , Carpenter-Warren , C , Anderson , N A & Watson , A J B 2019 , ' A cascade Suzuki-Miyaura/Diels-Alder protocol : exploring the bifunctional utility of vinyl Bpin ' , Synlett , vol. 30 , no. 7 , pp. 787-791 . https://doi.org/10.1055/s-0037-1611228en
dc.identifier.issn0936-5214
dc.identifier.otherORCID: /0000-0002-1582-4286/work/56639188
dc.identifier.urihttps://hdl.handle.net/10023/18752
dc.descriptionFunding: Industrial CASE studentship awarded from EPSRC and GlaxoSmithKline. The authors thank the EPSRC, GlaxoSmithKline, and the University of St Andrews for studentship funding (DLC), and the University of St Andrews and the EPSRC UK National Mass Spectrometry Facility at Swansea University for analyses.en
dc.description.abstractCascade reactions are an important strategy in reaction design, allowing streamlining of chemical synthesis. Here we report a cascade Suzuki-Miyaura/Diels-Alder reaction, employing vinyl Bpin as a bifunctional reagent in two distinct roles: as an organoboron nucleophile for cross- coupling and as a Diels-Alder dienophile. Merging these two reactions enables a rapid and operationally simple synthesis of functionalized carbocycles in good yield. The effect of the organoboron subtype on Diels- Alder regioselectivity was investigated and post-synthetic modifications were carried out on a model substrate. The potential for a complementary Heck/Diels-Alder process was also assessed.
dc.format.extent5
dc.format.extent564065
dc.language.isoeng
dc.relation.ispartofSynletten
dc.subjectBpinen
dc.subjectCascadeen
dc.subjectCross-couplingen
dc.subjectDiels-Alderen
dc.subjectSuzuki-Miyauraen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subject.lccQDen
dc.titleA cascade Suzuki-Miyaura/Diels-Alder protocol : exploring the bifunctional utility of vinyl Bpinen
dc.typeJournal articleen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doi10.1055/s-0037-1611228
dc.description.statusPeer revieweden
dc.date.embargoedUntil2019-10-24
dc.identifier.urlhttps://www.thieme-connect.de/media/synlett/EFirst/supmat/sup_st-2018-d0578-l_10-1055_s-0037-1611228.pdfen


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