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Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/18108
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dc.contributor.authorStockton, Kieranen
dc.contributor.authorMerritt, Christopheren
dc.contributor.authorSumby, Christopher Jen
dc.contributor.authorGreatrex, Benen
dc.date.accessioned2015-11-06T11:20:00Z-
dc.date.issued2015-
dc.identifier.citationEuropean Journal of Organic Chemistry, 2015(32), p. 6999-7008en
dc.identifier.issn1099-0690en
dc.identifier.issn1434-193Xen
dc.identifier.urihttps://hdl.handle.net/1959.11/18108-
dc.description.abstractThe chiral pool material (-)-levoglucosenone (6,8-dioxabicyclo[3.2.1]oct-2-en-4-one, LGO) has been substituted by using a series of Pd-mediated cross-coupling reactions. Iodination of LGO followed by Suzuki-Miyaura cross-coupling reaction with boronic acids by employing the Buchwald ligand SPhos with Pd(OAc)₂ afforded 3-aryl derivatives in excellent yields. Selective Heck arylation reaction at the 2-position was achieved with aryl iodides with K₃PO₄ as base and SPhos ligand with Pd(OAc)₂ (1-5 mol-%). A selective hydroarylation reaction (formal conjugate addition) was developed by using the same aryl iodides, benzyldiethylamine, Pd-(OAc)₂, and P(o-tol)₃. The products were converted, either directly or after alkene reduction, through a Baeyer-Villiger oxidation into chiral 3- and 4-substituted 5-(hydroxymethyl)-dihydrofuran-2(3H)-ones.en
dc.languageenen
dc.publisherWiley-VCH Verlag GmbH & Co KGaAen
dc.relation.ispartofEuropean Journal of Organic Chemistryen
dc.titlePalladium-Catalyzed Suzuki-Miyaura, Heck and Hydroarylation Reactions on (-)-Levoglucosenone and Application to the Synthesis of Chiral y-Butyrolactonesen
dc.typeJournal Articleen
dc.identifier.doi10.1002/ejoc.201501083en
dc.subject.keywordsBiologically Active Moleculesen
dc.subject.keywordsOrganic Chemical Synthesisen
dc.subject.keywordsOrganic Green Chemistryen
local.contributor.firstnameKieranen
local.contributor.firstnameChristopheren
local.contributor.firstnameChristopher Jen
local.contributor.firstnameBenen
local.subject.for2008030401 Biologically Active Moleculesen
local.subject.for2008030503 Organic Chemical Synthesisen
local.subject.for2008030504 Organic Green Chemistryen
local.subject.seo2008970103 Expanding Knowledge in the Chemical Sciencesen
local.subject.seo2008860899 Human Pharmaceutical Products not elsewhere classifieden
local.profile.schoolIT Voice Systemsen
local.profile.schoolSchool of Rural Medicineen
local.profile.emailkstockt2@une.edu.auen
local.profile.emailcmerrit4@une.edu.auen
local.profile.emailbgreatre@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.identifier.epublicationsrecordune-20151102-162454en
local.publisher.placeGermanyen
local.format.startpage6999en
local.format.endpage7008en
local.identifier.scopusid84946224835en
local.peerreviewedYesen
local.identifier.volume2015en
local.identifier.issue32en
local.contributor.lastnameStocktonen
local.contributor.lastnameMerritten
local.contributor.lastnameSumbyen
local.contributor.lastnameGreatrexen
dc.identifier.staffune-id:kstockt2en
dc.identifier.staffune-id:cmerrit4en
dc.identifier.staffune-id:bgreatreen
local.profile.orcid0000-0002-0356-4966en
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:18314en
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
local.title.maintitlePalladium-Catalyzed Suzuki-Miyaura, Heck and Hydroarylation Reactions on (-)-Levoglucosenone and Application to the Synthesis of Chiral y-Butyrolactonesen
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.search.authorStockton, Kieranen
local.search.authorMerritt, Christopheren
local.search.authorSumby, Christopher Jen
local.search.authorGreatrex, Benen
local.uneassociationUnknownen
local.identifier.wosid000364532000005en
local.year.published2015en
local.subject.for2020340401 Biologically active moleculesen
local.subject.for2020340503 Organic chemical synthesisen
local.subject.for2020340504 Organic green chemistryen
local.subject.seo2020280105 Expanding knowledge in the chemical sciencesen
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