Resolution of trans-2-azidocycloalkanols by separation of their mandelic acid esters

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dc.authoridYESIL, Tolga Acar/0000-0001-5983-8447
dc.contributor.authorYesil, Tolga A.
dc.contributor.authorYavuz, Mustafa
dc.contributor.authorErturk, Erkan
dc.date.accessioned2025-03-23T19:37:45Z
dc.date.available2025-03-23T19:37:45Z
dc.date.issued2023
dc.departmentSinop Üniversitesi
dc.description.abstractIt is presented that resolution of (+/-)-trans-2-azidocylohexanol and (+/-)-trans-2-azidocyclooctanol can be effected with (R)-mandelic acid. (R)-Mandelate esters of these azido alcohols can be separated by column chromatog-raphy on silica gel in an efficient manner. Upon methanolysis (transesterification) of the diastereomerically pure (R)-mandelate esters by K2CO3, enantiomerically pure trans-2-azidocylohexanols and trans-2-azidocyclooctanols are obtained. Their synthetic relevance has been also demonstrated by subjecting them to some enantiospecific transformations, such as the Mitsunobu reaction and hydrogenolysis of the azide functionality. Notably, this is the first study reporting the preparation of enantiopure trans-2-azidocyclooctanols.
dc.description.sponsorshipScientific and Technological Research Council of Turkey
dc.description.sponsorshipThe authors declare the following financial interests/personal re- lationships which may be considered as potential competing interests: Erkan Erturk reports a relationship with Scientific and Technological Research Council of Turkey that includes: employment.
dc.identifier.doi10.1016/j.tetlet.2023.154828
dc.identifier.issn0040-4039
dc.identifier.issn1873-3581
dc.identifier.scopus2-s2.0-85178958155
dc.identifier.scopusqualityQ3
dc.identifier.urihttps://doi.org/10.1016/j.tetlet.2023.154828
dc.identifier.urihttps://hdl.handle.net/11486/6002
dc.identifier.volume133
dc.identifier.wosWOS:001113804100001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofTetrahedron Letters
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectAzides
dc.subjectAzido alcohols
dc.subjectChiral resolution
dc.subjectResolution with mandelic acid
dc.subjectResolution oftrans-2-azidocycloalkanols
dc.subjectAsymmetric synthesis
dc.titleResolution of trans-2-azidocycloalkanols by separation of their mandelic acid esters
dc.typeArticle

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