Carboxylate ion dependency in the Cu(II) catalysed asymmetric Henry reaction: Structural characterisation of a tridentate Schiff base complex containing a coordinated carboxylic acid

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dc.contributor.authorAkinci, Arzu
dc.contributor.authorCelepci, Duygu Barut
dc.contributor.authorKaradeniz, Leman
dc.contributor.authorKorkmaz, Neslihan
dc.contributor.authorAygun, Muhittin
dc.contributor.authorAstley, Stephen T.
dc.date.accessioned2019-10-27T10:47:29Z
dc.date.available2019-10-27T10:47:29Z
dc.date.issued2017
dc.departmentEge Üniversitesien_US
dc.description.abstractSix tridentate Schiff base ligands containing tertiary butyl or benzyl substituents were prepared from chiral amino alcohols and salicylaldehyde derivatives. The ligands were employed as catalysts for the Cu(II) catalysed asymmetric Henry reaction. It was discovered that when different carboxylate salts were used instead of copper acetate as the Cu(II) salt, significant changes in the enantioselectivity of the reactions were observed. Addition of Cu(OAc)(2) to the ligand prepared from salicylaldehyde and a, a-diphenyl-tert-leucinol resulted in the formation of dark green crystals. X-ray structural analysis of these crystals showed that a square planar monomeric complex had been formed rather than the expected dimer. In the structure, the copper(II) centre is bonded to the tridentate ONO ligand and an acetate ion. There is a strong hydrogen bond between the protonated alcoholic oxygen of the Schiff base ligand and the uncoordinated acetate oxygen atom. These results, taken together, indicate that the carboxylate anion may be an important part of the active intermediate when this type of copper complex is used as a catalyst in the asymmetric Henry reaction.en_US
dc.description.sponsorshipEge Universitesi [15-FEN-035]; Dokuz Eylul UniversitesiDokuz Eylul University [2010.KB.FEN.13]en_US
dc.description.sponsorshipEge Universitesi, Grant/Award Number: 15-FEN-035; Dokuz Eylul Universitesi, Grant/Award Number: 2010.KB.FEN.13en_US
dc.identifier.doi10.1002/aoc.3831
dc.identifier.issn0268-2605
dc.identifier.issn1099-0739
dc.identifier.issn0268-2605en_US
dc.identifier.issn1099-0739en_US
dc.identifier.issue12en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1002/aoc.3831
dc.identifier.urihttps://hdl.handle.net/11454/31429
dc.identifier.volume31en_US
dc.identifier.wosWOS:000419195800019en_US
dc.identifier.wosqualityQ1en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.ispartofApplied Organometallic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectasymmetric Henry reactionen_US
dc.subjectchiral copper (II) catalysten_US
dc.subjectcrystal structureen_US
dc.subjectintramolecular hydrogen bonden_US
dc.subjectSchiff base complexen_US
dc.titleCarboxylate ion dependency in the Cu(II) catalysed asymmetric Henry reaction: Structural characterisation of a tridentate Schiff base complex containing a coordinated carboxylic aciden_US
dc.typeArticleen_US

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