Asymmetric Organocatalytic Efficiency of Synthesized Chiral ?-Amino Alcohols in Ring-Opening of Glycidol with Phenols

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dc.contributor.authorAral, Tarik
dc.contributor.authorKarakaplan, Mehmet
dc.contributor.authorHosgoren, Halil
dc.date.accessioned2024-04-24T16:02:07Z
dc.date.available2024-04-24T16:02:07Z
dc.date.issued2012
dc.departmentDicle Üniversitesien_US
dc.description.abstractA series of novel chiral beta-amino alcohols 3-5 and 7-10 were synthesized by regioselective ring opening of epoxides and chiral amines with a straightforward method in high yields (up to 99 %). Kinetic resolution of racemic glycidol with phenols was achieved by using chiral amino alcohols as organocatalysts. Amino alcohols 5, 8 and 10 exhibited the highest enantioselectivities with p-cresol, phenol, and p-methoxyphenol by 63, 65, 58 % ee, respectively. The moderate enantioselectivities were observed with catalyst 9b towards all the nucleophiles (34-48 % ee). The ee values of the desired 3-aryloxy-1,2-diols were determined by HPLC. This study presents an attractive tool for the synthesis of beta-blockers and structurally complex molecules.en_US
dc.description.sponsorshipResearch Project Council of Dicle University [DUBAP-08-FF-13]; Scientific and Technological Research Council of Turkey (TUBITAK) [110T468]en_US
dc.description.sponsorshipWe thank the Research Project Council of Dicle University (DUBAP-08-FF-13) and the Scientific and Technological Research Council of Turkey (TUBITAK) (Project no: 110T468) for their financial support.en_US
dc.identifier.doi10.1007/s10562-012-0814-4
dc.identifier.endpage802en_US
dc.identifier.issn1011-372X
dc.identifier.issn1572-879X
dc.identifier.issue6en_US
dc.identifier.scopus2-s2.0-84861577151
dc.identifier.scopusqualityQ2
dc.identifier.startpage794en_US
dc.identifier.urihttps://doi.org/10.1007/s10562-012-0814-4
dc.identifier.urihttps://hdl.handle.net/11468/14635
dc.identifier.volume142en_US
dc.identifier.wosWOS:000304401600017
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherSpringeren_US
dc.relation.ispartofCatalysis Letters
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectEpoxide Ring Openingen_US
dc.subjectBeta-Amino Alcoholsen_US
dc.subjectKinetic Resolutionen_US
dc.subjectOrganocatalystsen_US
dc.subject3-Aryloxy-1,2-Propanediolsen_US
dc.titleAsymmetric Organocatalytic Efficiency of Synthesized Chiral ?-Amino Alcohols in Ring-Opening of Glycidol with Phenolsen_US
dc.titleAsymmetric Organocatalytic Efficiency of Synthesized Chiral ?-Amino Alcohols in Ring-Opening of Glycidol with Phenols
dc.typeArticleen_US

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