New functional chiral P-based ligands and application in ruthenium-catalyzed enantioselective transfer hydrogenation of ketones

Basit Öğe Kaydı
dc.authoridKayan, Cezmi/0000-0001-5700-8546
dc.authoridGurbuz, Nevin/0000-0003-3201-3597
dc.authoridbinbay, nil ertekin/0000-0002-2488-0378
dc.authoridAydemir, Murat/0000-0002-4238-5012
dc.authorwosidKayan, Cezmi/AAC-1876-2021
dc.authorwosidGurbuz, Nevin/A-3069-2016
dc.authorwosidmeric, nermin/AAT-9164-2021
dc.authorwosidbinbay, nil ertekin/C-8039-2019
dc.contributor.authorMeric, Nermin
dc.contributor.authorKayan, Cezmi
dc.contributor.authorGurbuz, Nevin
dc.contributor.authorKarakaplan, Mehmet
dc.contributor.authorBinbay, Nil Ertekin
dc.contributor.authorAydemir, Murat
dc.date.accessioned2024-08-04T20:44:05Z
dc.date.available2024-08-04T20:44:05Z
dc.date.issued2017
dc.departmentİnönü Üniversitesien_US
dc.description.abstractMetal-catalyzed asymmetric transfer hydrogenation is a powerful and practical method for the reduction of ketones to produce the corresponding secondary alcohols, which are valuable building blocks in the pharmaceutical, perfume, and agrochemical industries. Hence, a series of novel chiral beta-amino alcohols were synthesized by chiral amines with regioselective ring opening of (S)-propylene oxide or reaction with (S)-(+)-2-hydroxypropyl p-toluenesulfonate by a straightforward method. The chiral ruthenium catalytic systems generated from [Ru(arene)(mu-Cl)Cl](2) complexes and chiral phosphinite ligands based on amino alcohol derivatives were employed in asymmetric transfer hydrogenation of ketones to give the corresponding optically active alcohols; (2S)-1-([(2.9-2-[(diphenylphosphanypoxylpropyl][(1R)-1-phenylethyl]amino}propan-2-yldiphenylphosphinitobis[dichol-oro(eta(6)-benzene)ruthenium(II)] acts an excellent catalyst in the reduction of cl-naphthyl methyl ketone, giving the corresponding alcohol with up to 99% ee. The substituents on the backbone of the ligands were found to have a remarkable effect on both the conversion and enantioselectivity of the catalysts. Furthermore, this transfer hydrogenation is characterized by low reversibility under these conditions. (C) 2017 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipTUBITAK [113Z297]en_US
dc.description.sponsorshipPartial support from TUBITAK (Project number: 113Z297) is gratefully acknowledged.en_US
dc.identifier.doi10.1016/j.tetasy.2017.10.004
dc.identifier.endpage1749en_US
dc.identifier.issn0957-4166
dc.identifier.issue12en_US
dc.identifier.scopus2-s2.0-85031794388en_US
dc.identifier.scopusqualityN/Aen_US
dc.identifier.startpage1739en_US
dc.identifier.urihttps://doi.org/10.1016/j.tetasy.2017.10.004
dc.identifier.urihttps://hdl.handle.net/11616/97999
dc.identifier.volume28en_US
dc.identifier.wosWOS:000418988400009en_US
dc.identifier.wosqualityN/Aen_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron-Asymmetryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectAsymmetric Transfer Hydrogenationen_US
dc.subjectDiels-Alder Reactionsen_US
dc.subjectAromatic Ketonesen_US
dc.subjectPhosphinite Ligandsen_US
dc.subjectCarbonyl-Compoundsen_US
dc.subjectHydride Complexesen_US
dc.subjectOrganic-Synthesisen_US
dc.subjectCrystal-Structureen_US
dc.subjectAmino-Alcoholsen_US
dc.subjectAreneen_US
dc.titleNew functional chiral P-based ligands and application in ruthenium-catalyzed enantioselective transfer hydrogenation of ketonesen_US
dc.typeArticleen_US

Dosyalar

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu