Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/19512
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dc.contributor.authorPeru, Aurelien A Men
dc.contributor.authorFlourat, Amandine Len
dc.contributor.authorGunawan, Christianen
dc.contributor.authorRaverty, Warwicken
dc.contributor.authorJevric, Martynen
dc.contributor.authorGreatrex, Benen
dc.contributor.authorAllais, Florenten
dc.date.accessioned2016-09-26T16:23:00Z-
dc.date.issued2016-
dc.identifier.citationMolecules, 21(8), p. 1-10en
dc.identifier.issn1420-3049en
dc.identifier.issn1431-5165en
dc.identifier.urihttps://hdl.handle.net/1959.11/19512-
dc.description.abstractChiral epoxides-such as ethyl and methyl (S)-3-(oxiran-2-yl)propanoates ((S)-1a/1b)-are valuable precursors in many chemical syntheses. Until recently, these compounds were synthesized from glutamic acid in four steps (deamination, reduction, tosylation and epoxide formation) in low to moderate overall yield (20%-50%). Moreover, this procedure requires some harmful reagents such as sodium nitrite ((eco)toxic) and borane (carcinogen). Herein, starting from levoglucosenone (LGO), a biobased chiral compound obtained through the flash pyrolysis of acidified cellulose, we propose a safer and more sustainable chemo-enzymatic synthetic pathway involving lipase-mediated Baeyer-Villiger oxidation, palladium-catalyzed hydrogenation, tosylation and treatment with sodium ethoxide/methoxide as key steps. This route afforded ethyl and methyl (S)-3-(oxiran-2-yl)propanoates in 57% overall yield, respectively. To demonstrate the potentiality of this new synthetic pathway from LGO, the synthesis of high value-added (S)-dairy lactone was undertaken from these epoxides and provided the target in 37% overall yield from LGO.en
dc.languageenen
dc.publisherMDPI AGen
dc.relation.ispartofMoleculesen
dc.titleChemo-Enzymatic Synthesis of Chiral Epoxides Ethyl and Methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable Levoglucosenone: An Access to Enantiopure (S)-Dairy Lactoneen
dc.typeJournal Articleen
dc.identifier.doi10.3390/molecules21080988en
dcterms.accessRightsGolden
dc.subject.keywordsOrganic Chemistryen
dc.subject.keywordsOrganic Green Chemistryen
dc.subject.keywordsOrganic Chemical Synthesisen
local.contributor.firstnameAurelien A Men
local.contributor.firstnameAmandine Len
local.contributor.firstnameChristianen
local.contributor.firstnameWarwicken
local.contributor.firstnameMartynen
local.contributor.firstnameBenen
local.contributor.firstnameFlorenten
local.subject.for2008030503 Organic Chemical Synthesisen
local.subject.for2008030599 Organic Chemistry not elsewhere classifieden
local.subject.for2008030504 Organic Green Chemistryen
local.subject.seo2008860604 Organic Industrial Chemicals (excl. Resins, Rubber and Plastics)en
local.subject.seo2008970103 Expanding Knowledge in the Chemical Sciencesen
local.profile.schoolSchool of Rural Medicineen
local.profile.emailbgreatre@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.identifier.epublicationsrecordune-20160901-142531en
local.publisher.placeSwitzerlanden
local.identifier.runningnumber988en
local.format.startpage1en
local.format.endpage10en
local.identifier.scopusid84982686515en
local.peerreviewedYesen
local.identifier.volume21en
local.identifier.issue8en
local.title.subtitleAn Access to Enantiopure (S)-Dairy Lactoneen
local.access.fulltextYesen
local.contributor.lastnamePeruen
local.contributor.lastnameFlouraten
local.contributor.lastnameGunawanen
local.contributor.lastnameRavertyen
local.contributor.lastnameJevricen
local.contributor.lastnameGreatrexen
local.contributor.lastnameAllaisen
dc.identifier.staffune-id:bgreatreen
local.profile.orcid0000-0002-0356-4966en
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:19704en
dc.identifier.academiclevelAcademicen
local.title.maintitleChemo-Enzymatic Synthesis of Chiral Epoxides Ethyl and Methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable Levoglucosenoneen
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.search.authorPeru, Aurelien A Men
local.search.authorFlourat, Amandine Len
local.search.authorGunawan, Christianen
local.search.authorRaverty, Warwicken
local.search.authorJevric, Martynen
local.search.authorGreatrex, Benen
local.search.authorAllais, Florenten
local.uneassociationUnknownen
local.identifier.wosid000382334600027en
local.year.published2016en
local.fileurl.closedpublishedhttps://rune.une.edu.au/web/retrieve/186745e2-2fd9-4fbc-8bbc-17a8ede11015en
local.subject.for2020340503 Organic chemical synthesisen
local.subject.for2020340504 Organic green chemistryen
local.subject.seo2020240908 Organic industrial chemicals (excl. resins, rubber and plastics)en
local.subject.seo2020280105 Expanding knowledge in the chemical sciencesen
Appears in Collections:Journal Article
School of Rural Medicine
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