A series of novel ?-hydroxyamide based catalysts for borane-mediated enantioselective reductions of prochiral ketones

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dc.contributor.authorAzizoglu, Murat
dc.contributor.authorErdogan, Asli
dc.contributor.authorArslan, Nevin
dc.contributor.authorTurgut, Yilmaz
dc.contributor.authorHosgoren, Halil
dc.contributor.authorPirinccioglu, Necmettin
dc.date.accessioned2024-04-24T16:18:28Z
dc.date.available2024-04-24T16:18:28Z
dc.date.issued2016
dc.departmentDicle Üniversitesien_US
dc.description.abstractThe enantioselective reduction of prochiral ketones with borane in the presence of a chiral ligand has received considerable attention. Hydroxylamine-based chiral ligands with amide and hydroxyl functions in the presence of other co-ordinating groups are highly effective in these asymmetric reductions. The current work presents a simple one step synthesis of a series of beta-hydroxyamide-based ligands from the reaction between 3-hydroxy-2-naphthoic acid and chiral amino alcohols and their applications as catalysts in asymmetric borane-mediated reductions of aromatic prochiral ketones in THE The reductions provided the corresponding secondary alcohols with up to 96% ee and in good to excellent yields (89-99%). OFF calculations at B3LYP/6-31+g(d) level offered theoretical models to account for the enantioselectivity imposed by the chiral ligands in the reductions of the ketones. (C) 2016 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [110 T 809]en_US
dc.description.sponsorshipWe would like to thank The Scientific and Technological Research Council of Turkey (TUBITAK) for financially supporting this research (Project No: 110 T 809).en_US
dc.identifier.doi10.1016/j.tetasy.2016.06.003
dc.identifier.endpage622en_US
dc.identifier.issn0957-4166
dc.identifier.issue14-15en_US
dc.identifier.scopus2-s2.0-84977098563
dc.identifier.scopusqualityN/A
dc.identifier.startpage614en_US
dc.identifier.urihttps://doi.org/10.1016/j.tetasy.2016.06.003
dc.identifier.urihttps://hdl.handle.net/11468/16115
dc.identifier.volume27en_US
dc.identifier.wosWOS:000380419800004
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron-Asymmetry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject[No Keyword]en_US
dc.titleA series of novel ?-hydroxyamide based catalysts for borane-mediated enantioselective reductions of prochiral ketonesen_US
dc.titleA series of novel ?-hydroxyamide based catalysts for borane-mediated enantioselective reductions of prochiral ketones
dc.typeArticleen_US

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