Proline-based organocatalyst-mediated asymmetric aldol reaction of acetone with substituted aromatic aldehydes: An experimental and theoretical study

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dc.authorid0000-0003-0142-9215en_US
dc.authorid0000-0001-9805-9745Birlikte çalıştığı yazarlarBirlikte çalıştığı kişileren_US
dc.contributor.authorArslan, Nevin
dc.contributor.authorErcan, Selami
dc.contributor.authorPirinççi̇oğlu, Necmettin
dc.date.accessioned2021-08-25T06:01:44Z
dc.date.available2021-08-25T06:01:44Z
dc.date.issued2020en_US
dc.departmentDicle Üniversitesi, Fen Fakültesi, Kimya Bölümüen_US
dc.description.abstractThis work involves a facile synthesis of three (S)-proline-based organocatalysts with C2 symmetry and their effects in enantioselective aldol reaction of acetone with substituted aromatic aldehydes. Moderate enantioselectivities (up to 61% ee) were obtained depending on the nature of the substituents on the aryl ring. Computational calculations at HF/6-31 + G(d) level were employed to underline the enantioselectivity imposed by all the organocatalysts. Higher calculations at B3LYP/6-311 ++ G(d,p) scrf=(solvent=dichloromethane)//B3LYP/6-31 + G(d) levels of theory were also performed for the aldol reaction of acetone with benzaldehyde and 4-nitrobenzaldehyde catalyzed by 1. The computational outcomes were consistent with those produced by experimental results and they were valuable to elucidate the mechanism for the observed stereoselectivity.en_US
dc.identifier.citationArslan, N., Ercan, S. ve Pirinççi̇oğlu, N. (2020). Proline-based organocatalyst-mediated asymmetric aldol reaction of acetone with substituted aromatic aldehydes: An experimental and theoretical study. Turkish Journal of Chemistry, 44(2), 335-351.en_US
dc.identifier.doi10.3906/KIM-1908-3
dc.identifier.endpage351en_US
dc.identifier.issn1300-0527
dc.identifier.issn1303-6130
dc.identifier.issue2en_US
dc.identifier.pmid33488161
dc.identifier.scopus2-s2.0-85085375089
dc.identifier.scopusqualityQ3
dc.identifier.startpage335en_US
dc.identifier.trdizinid335244
dc.identifier.urihttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7671204/
dc.identifier.urihttps://hdl.handle.net/11468/7384
dc.identifier.urihttps://search.trdizin.gov.tr/yayin/detay/335244
dc.identifier.volume44en_US
dc.identifier.wosWOS:000522796000006
dc.identifier.wosqualityQ4
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.indekslendigikaynakTR-Dizin
dc.institutionauthorArslan, Nevin
dc.institutionauthorPirinççi̇oğlu, Necmettin
dc.language.isoenen_US
dc.publisherTUBITAKen_US
dc.relation.ispartofTurkish Journal of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectAcetoneen_US
dc.subjectAldol reactionen_US
dc.subjectComputational modellingen_US
dc.subjectEnantioselectivityen_US
dc.subjectOrganocatalysisen_US
dc.subjectProlineen_US
dc.subjectSubstituted aldehydesen_US
dc.titleProline-based organocatalyst-mediated asymmetric aldol reaction of acetone with substituted aromatic aldehydes: An experimental and theoretical studyen_US
dc.titleProline-based organocatalyst-mediated asymmetric aldol reaction of acetone with substituted aromatic aldehydes: An experimental and theoretical study
dc.typeArticleen_US

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