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Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/29369
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dc.contributor.authorLedingham, Edward Ten
dc.contributor.authorGreatrex, Ben Wen
dc.date.accessioned2020-09-02T02:20:07Z-
dc.date.available2020-09-02T02:20:07Z-
dc.date.issued2019-02-06-
dc.identifier.citationAustralian Journal of Chemistry, 72(5), p. 362-368en
dc.identifier.issn1445-0038en
dc.identifier.issn0004-9425en
dc.identifier.urihttps://hdl.handle.net/1959.11/29369-
dc.description.abstractEfficient conditions have been developed for the diastereoselective aziridination of the biomass pyrolysis product (−)-levoglucosenone, via the reaction of primary aliphatic amines with 3-iodolevoglucosenone. In contrast to the reactions of aliphatic amines, the use of 4-methoxyaniline resulted in an aza-Michael-initiated dimerisation reaction, and 1,3-diphenylurea gave a 2-imidazolidinone. The aziridine products were transformed using the aza-Wharton reaction, affording novel sulfonamide and amine-substituted 6,8-dioxabicyclo[3.2.1]oct-3-enes with potential as sp<sup>3</sup>-rich chiral scaffolds.en
dc.languageenen
dc.publisherCSIRO Publishingen
dc.relation.ispartofAustralian Journal of Chemistryen
dc.titleAziridination and aza-Wharton Reactions of Levoglucosenoneen
dc.typeJournal Articleen
dc.identifier.doi10.1071/CH18574en
local.contributor.firstnameEdward Ten
local.contributor.firstnameBen Wen
local.subject.for2008030503 Organic Chemical Synthesisen
local.subject.seo2008970103 Expanding Knowledge in the Chemical Sciencesen
local.profile.schoolSchool of Rural Medicineen
local.profile.schoolSchool of Rural Medicineen
local.profile.emaileleding2@une.edu.auen
local.profile.emailbgreatre@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.publisher.placeAustraliaen
local.format.startpage362en
local.format.endpage368en
local.identifier.scopusid85061266630en
local.peerreviewedYesen
local.identifier.volume72en
local.identifier.issue5en
local.contributor.lastnameLedinghamen
local.contributor.lastnameGreatrexen
dc.identifier.staffune-id:eleding2en
dc.identifier.staffune-id:bgreatreen
local.profile.orcid0000-0002-0356-4966en
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:1959.11/29369en
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
local.title.maintitleAziridination and aza-Wharton Reactions of Levoglucosenoneen
local.relation.fundingsourcenoteAustralian Government Research Training Program (RTP) Scholarshipen
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.search.authorLedingham, Edward Ten
local.search.authorGreatrex, Ben Wen
local.uneassociationYesen
local.atsiresearchNoen
local.sensitive.culturalNoen
local.identifier.wosid000467283100006en
local.year.published2019en
local.fileurl.closedpublishedhttps://rune.une.edu.au/web/retrieve/bf80d099-e4ba-40bc-b0a9-fb2689512332en
local.subject.for2020340503 Organic chemical synthesisen
local.subject.seo2020280105 Expanding knowledge in the chemical sciencesen
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School of Rural Medicine
School of Science and Technology
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