Please use this identifier to cite or link to this item: https://hdl.handle.net/11147/14242
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dc.contributor.authorKuş, Melih-
dc.contributor.authorOmur, Cenk-
dc.contributor.authorKaraca, Sila-
dc.contributor.authorArtok, Levent-
dc.date.accessioned2024-01-30T09:24:38Z-
dc.date.available2024-01-30T09:24:38Z-
dc.date.issued2023-
dc.identifier.issn2624-8549-
dc.identifier.urihttps://doi.org/10.3390/chemistry5040173-
dc.identifier.urihttps://hdl.handle.net/11147/14242-
dc.description.abstractThe iron-promoted 1,5-substitution reaction of endocyclic oxiranes with MeMgBr yields exocyclic 2,4,5-trienols with high diastereomeric ratios of up to 100:0. However, for the method's success, the oxirane ring must have a trans-configuration. The reactions exhibit strong stereoselectivity concerning the methylation mode and the configuration of the resulting exocyclic double bond. Enantiomerically pure enyne oxiranes can be synthesized through Sharpless asymmetric dihydroxylation and subsequent manipulations. With these reagents, it has been possible to produce exocyclic 2,4,5-trienols in enantiopure forms. Importantly, this process maintains chirality without degradation during the center-to-axis transfer of chirality.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey [117Z299]; IZTECH Scientific Research Projects Coordinatorship [2017IYTE85]en_US
dc.description.sponsorshipThis work was financially supported by the Scientific and Technological Research Council of Turkey (117Z299) and IZTECH Scientific Research Projects Coordinatorship (2017IYTE85).en_US
dc.language.isoenen_US
dc.publisherMDPIen_US
dc.relation.ispartofChemistry-Switzerlanden_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectenyne oxiranesen_US
dc.subjectvinylallenesen_US
dc.subject2,4,5-trienolsen_US
dc.subjectiron-catalyzeden_US
dc.subject1,5-substitutionen_US
dc.subjectenantiopure allenesen_US
dc.subjectPalladium-Catalyzed Alkoxycarbonylationen_US
dc.subjectElectrocyclic Ring-Closureen_US
dc.subjectEnantioselective Synthesisen_US
dc.subjectAsymmetric Epoxidationen_US
dc.subjectGrignard-Reagentsen_US
dc.subjectDiastereoselective Methoden_US
dc.subjectPropargyl Carboxylatesen_US
dc.subjectConjugate Additionen_US
dc.subjectCoupling Reactionsen_US
dc.subjectHydrogen Shiftsen_US
dc.titleIron-Promoted 1,5-Substitution Reaction of Endocyclic Enyne Oxiranes with MeMgBr: A Stereoselective Method for the Synthesis of Exocyclic 2,4,5-Trienol Derivativesen_US
dc.typeArticleen_US
dc.authoridKARACA, SILA/0009-0007-6929-1853-
dc.institutionauthor-
dc.departmentİzmir Institute of Technologyen_US
dc.identifier.volume5en_US
dc.identifier.issue4en_US
dc.identifier.startpage2682en_US
dc.identifier.endpage2699en_US
dc.identifier.wosWOS:001131213200001en_US
dc.identifier.scopus2-s2.0-85180697345en_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.identifier.doi10.3390/chemistry5040173-
dc.authorscopusid35190558000-
dc.authorscopusid58782667300-
dc.authorscopusid35097521000-
dc.authorscopusid6603902973-
dc.authorwosidKARACA, SILA/JSL-2721-2023-
item.grantfulltextnone-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.fulltextNo Fulltext-
item.languageiso639-1en-
item.openairetypeArticle-
item.cerifentitytypePublications-
crisitem.author.dept04.01. Department of Chemistry-
crisitem.author.dept04.01. Department of Chemistry-
Appears in Collections:Scopus İndeksli Yayınlar Koleksiyonu / Scopus Indexed Publications Collection
WoS İndeksli Yayınlar Koleksiyonu / WoS Indexed Publications Collection
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