Asymmetric organocatalytic efficiency of synthesized chiral β-amino alcohols in ring-opening of glycidol with phenols

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dc.contributor.authorAral, Tarık
dc.contributor.authorKarakaplan, Mehmet
dc.contributor.authorHoşgören, Halil
dc.date.accessioned2019-06-21T12:28:14Z
dc.date.available2019-06-21T12:28:14Z
dc.date.issued2012-04-11en_US
dc.departmentBatman Üniversitesi Fen - Edebiyat Fakültesi Kimya Bölümüen_US
dc.description.abstractA series of novel chiral β-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 β-blockers and structurally complex molecules.en_US
dc.identifier.citationAral, T., Karakaplan, M., & Hoşgören, H. (2012).Asymmetric organocatalytic efficiency of synthesized chiral β-amino alcohols in ring-opening of glycidol with phenols. Catalysis Letters, 142(6), pp. 794-802. https://doi.org/10.1007/s10562-012-0814-4en_US
dc.identifier.endpage802en_US
dc.identifier.issn1011-372X
dc.identifier.issn1572-879X
dc.identifier.issue6en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage794en_US
dc.identifier.urihttps://doi.org/10.1007/s10562-012-0814-4
dc.identifier.urihttps://hdl.handle.net/20.500.12402/2104
dc.identifier.volume142en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherSpringer Natureen_US
dc.relation.isversionof10.1007/s10562-012-0814-4en_US
dc.relation.journalCatalysis Lettersen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.rightsAttribution-NonCommercial-ShareAlike 3.0 United States*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/3.0/us/*
dc.subjectβ-Amino Alcoholsen_US
dc.subject3-Aryloxy-1,2-Propanediolsen_US
dc.subjectEpoxide Ring Openingen_US
dc.subjectKinetic Resolutionen_US
dc.subjectOrganocatalystsen_US
dc.titleAsymmetric organocatalytic efficiency of synthesized chiral β-amino alcohols in ring-opening of glycidol with phenolsen_US
dc.typeArticleen_US

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