An Insight into the Asymmetric Resolution of 1-Aminoindane Derivatives

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dc.contributor.authorAkincioglu, Akin
dc.contributor.authorAkbaba, Yusuf
dc.contributor.authorKose, Leyla Polat
dc.contributor.authorGoksu, Suleyman
dc.date.accessioned2024-03-13T10:30:39Z
dc.date.available2024-03-13T10:30:39Z
dc.date.issued2023
dc.departmentİstanbul Beykent Üniversitesien_US
dc.description.abstractCompounds with 1-aminoindane motif exhibit vital biological activities in the central nervous system. Therefore, it is very important to synthesize new compounds with this moiety and to obtain them in high enantiopurity. In this study, novel substituted 1-aminoindane derivatives were synthesized, and their asymmetric resolutions were carried out. Accordingly, the reduction of 1-indanones with NaBH4, conversion of alcohols to azides via an alternative Mitsunobu reaction followed by reduction of azides afforded (+/-)-1-aminoindane hydrochloride or hydrobromide salts. Amine salts were converted into their free amines by using excess amount of Et3N and then in situ occurred free (+/-)-amines were reacted with (R)-O-acetylmandeloyl chloride to give diastereomeric mixtures. The crystallization of the diastereomeric mixtures followed by hydrolysis yielded the corresponding asymmetric amines with high enantio-purity.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkiye (TUBITAK) [TBAG-109T241]; Ataturk Universityen_US
dc.description.sponsorshipAcknowledgments We are greatly indebted to The Scientific and Technological Research Council of Turkiye (TUBITAK, Grant no. TBAG-109T241) and Ataturk University for their financial supports of this work.en_US
dc.identifier.doi10.1002/slct.202300278
dc.identifier.issn2365-6549
dc.identifier.issue17en_US
dc.identifier.scopus2-s2.0-85159799957en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.urihttps://doi.org/10.1002/slct.202300278
dc.identifier.urihttps://hdl.handle.net/20.500.12662/3465
dc.identifier.volume8en_US
dc.identifier.wosWOS:000979905500001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherWiley-V C H Verlag Gmbhen_US
dc.relation.ispartofChemistryselecten_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject1-aminoindaneen_US
dc.subjectasymmetric resolutionen_US
dc.subjectdiastereomersen_US
dc.subjectenantio-pureen_US
dc.subjectO-acetylmandeloyl chlorideen_US
dc.titleAn Insight into the Asymmetric Resolution of 1-Aminoindane Derivativesen_US
dc.typeArticleen_US

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