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Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/26829
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dc.contributor.authorKlepp, Julianen
dc.contributor.authorSumby, Christopher Jen
dc.contributor.authorGreatrex, Ben Wen
dc.date.accessioned2019-05-06T04:47:45Z-
dc.date.available2019-05-06T04:47:45Z-
dc.date.issued2018-
dc.identifier.citationSynlett, 29(11), p. 1441-1446en
dc.identifier.issn1437-2096en
dc.identifier.issn0936-5214en
dc.identifier.urihttps://hdl.handle.net/1959.11/26829-
dc.description.abstractA new family of chiral auxiliaries has been developed based on the lignocellulosic biomass pyrolysis product levoglucosenone. A promising single stereoisomer with an alcohol and π-stacking phenyl substituents was prepared in excellent yield in two steps from di­hydrolevoglucosenone without chromatography on >50 g scale. Acrylate esters prepared from the auxiliaries underwent diastereoselective Lewis acid promoted Diels–Alder reactions with cyclopentadiene (­endo/exo 98:2, endo d.r. up to 98:2), dimethylbutadiene (d.r. 93:7), and isoprene (d.r. > 98:2)en
dc.languageenen
dc.publisherGeorg Thieme Verlagen
dc.relation.ispartofSynletten
dc.titleSynthesis of a Chiral Auxiliary Family from Levoglucosenone and Evaluation in the Diels–Alder Reactionen
dc.typeJournal Articleen
dc.identifier.doi10.1055/s-0037-1610148en
local.contributor.firstnameJulianen
local.contributor.firstnameChristopher Jen
local.contributor.firstnameBen Wen
local.subject.for2008030503 Organic Chemical Synthesisen
local.subject.for2008030504 Organic Green Chemistryen
local.subject.seo2008970103 Expanding Knowledge in the Chemical Sciencesen
local.subject.seo2008860604 Organic Industrial Chemicals (excl. Resins, Rubber and Plastics)en
local.subject.seo2008860899 Human Pharmaceutical Products not elsewhere classifieden
local.profile.schoolSchool of Science and Technologyen
local.profile.schoolSchool of Rural Medicineen
local.profile.emailjklepp3@une.edu.auen
local.profile.emailbgreatre@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.publisher.placeGermanyen
local.format.startpage1441en
local.format.endpage1446en
local.identifier.scopusid85047983468en
local.peerreviewedYesen
local.identifier.volume29en
local.identifier.issue11en
local.contributor.lastnameKleppen
local.contributor.lastnameSumbyen
local.contributor.lastnameGreatrexen
dc.identifier.staffune-id:jklepp3en
dc.identifier.staffune-id:bgreatreen
local.profile.orcid0000-0002-0356-4966en
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:1959.11/26829en
local.date.onlineversion2018-05-25-
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
local.title.maintitleSynthesis of a Chiral Auxiliary Family from Levoglucosenone and Evaluation in the Diels–Alder Reactionen
local.relation.fundingsourcenoteIPRA scholarship and the University of New Englanden
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.search.authorKlepp, Julianen
local.search.authorSumby, Christopher Jen
local.search.authorGreatrex, Ben Wen
local.uneassociationUnknownen
local.identifier.wosid000435602300006en
local.year.available2018en
local.year.published2018en
local.fileurl.closedpublishedhttps://rune.une.edu.au/web/retrieve/f1fec5d4-e3ca-406f-b7fc-613c9eea5fb7en
local.subject.for2020340503 Organic chemical synthesisen
local.subject.for2020340504 Organic green chemistryen
local.subject.seo2020280105 Expanding knowledge in the chemical sciencesen
local.subject.seo2020240908 Organic industrial chemicals (excl. resins, rubber and plastics)en
Appears in Collections:Journal Article
School of Rural Medicine
School of Science and Technology
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