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Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone

Ma, Xinghua; Liu, Xin; Yates, Patrick; Raverty, Warwick; Banwell, Martin; Ma, Chenxi; Willis, Anthony; Carr, Paul D.

Description

The manipulation of the enone moiety associated with the biomass-derived, homochiral and now abundant compound levoglucosenone (1) is described. While the trichloroacetimidates derived from the allylic alcohols 3 and 4 failed to engage in Overman-type rearrangements, certain ester derivatives reacted in the presence of Pd[0]-catalysts to give regio-isomeric mixtures of β,γ-unsaturated malonates or ketones, the structures of which were confirmed by single-crystal X-ray analyses. In other...[Show more]

dc.contributor.authorMa, Xinghua
dc.contributor.authorLiu, Xin
dc.contributor.authorYates, Patrick
dc.contributor.authorRaverty, Warwick
dc.contributor.authorBanwell, Martin
dc.contributor.authorMa, Chenxi
dc.contributor.authorWillis, Anthony
dc.contributor.authorCarr, Paul D.
dc.date.accessioned2019-07-09T05:49:59Z
dc.identifier.issn0040-4020
dc.identifier.urihttp://hdl.handle.net/1885/164500
dc.description.abstractThe manipulation of the enone moiety associated with the biomass-derived, homochiral and now abundant compound levoglucosenone (1) is described. While the trichloroacetimidates derived from the allylic alcohols 3 and 4 failed to engage in Overman-type rearrangements, certain ester derivatives reacted in the presence of Pd[0]-catalysts to give regio-isomeric mixtures of β,γ-unsaturated malonates or ketones, the structures of which were confirmed by single-crystal X-ray analyses. In other sequences involving 1,3-transposition reactions, an operationally simple means for converting compound 1 into isolevoglucosenone (2) is described.
dc.description.sponsorshipThis research was part-funded by Circa Group Pty Ltd. We thank the Institute of Advanced Studies for financial support while XL is the grateful recipient of a PhD Scholarship provided by Circa Group Pty Ltd. A/Professor Rod Bates (Nanyang Technological University, Singapore) is thanked for useful discussions.
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherElsevier
dc.rights© 2018 Elsevier Ltd.
dc.sourceTetrahedron
dc.subjectIsolevoglucosenone
dc.subjectLevoglucoseone
dc.subject1,3-Transposition
dc.subjectTsuji-Trost reaction
dc.subjectUnsaturated esters
dc.titleManipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume74
dcterms.dateAccepted2018-03-09
dc.date.issued2018-03-24
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationa383154xPUB10549
local.publisher.urlhttps://www.sciencedirect.com
local.type.statusPublished Version
local.contributor.affiliationMa, Xinghua, College of Science, ANU
local.contributor.affiliationLiu, Xin, College of Science, ANU
local.contributor.affiliationYates, Patrick, College of Science, ANU
local.contributor.affiliationRaverty, Warwick, Circa Group Pty Ltd
local.contributor.affiliationBanwell, Martin, College of Science, ANU
local.contributor.affiliationMa, Chenxi, College of Science, ANU
local.contributor.affiliationWillis, Anthony, College of Science, ANU
local.contributor.affiliationCarr, Paul D, College of Science, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue38
local.bibliographicCitation.startpage5000
local.bibliographicCitation.lastpage5011
local.identifier.doi10.1016/j.tet.2018.03.023
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2019-03-31T07:18:03Z
local.identifier.scopusID2-s2.0-85048548387
CollectionsANU Research Publications

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