Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst

Basit Öğe Kaydı
dc.authorid0000-0003-2380-7942
dc.contributor.authorSusam, Zeynep Dilşad
dc.contributor.authorBozdemir, Merve
dc.contributor.authorGündoğdu, Gülsüm
dc.date.accessioned2022-05-17T10:58:26Z
dc.date.available2022-05-17T10:58:26Z
dc.date.issued2022
dc.departmentTAÜ, Fen Fakültesi, Enerji Bilimi ve Teknolojileri Bölümüen_US
dc.description.abstractAsymmetric organocatalytic domino type Michael-S(N)2 reactions give access to enantiomerically enriched dihydrofuran derivatives that can be used as valuable chiral building blocks. A variety of alpha-bromonitroalkenes and 1,3-dicarbonyl compounds were allowed to react under optimized conditions, in the presence of a bifunctional quinine-derived sterically encumbered squaramide (H-bond donor) organocatalyst. The conditions developed in this article have great advantages over the methods known in the literature in terms of reaction duration (1-6 h vs. 24-96 h) and reaction temperature (room temperature vs. -20 degrees C to -50 degrees C) giving rise to quite diastereoselective products with good enantioselectivities up to 97% ee.
dc.identifier.citationAsymmetric organocatalytic domino type Michael-S(N)2 reactions give access to enantiomerically enriched dihydrofuran derivatives that can be used as valuable chiral building blocks. A variety of alpha-bromonitroalkenes and 1,3-dicarbonyl compounds were allowed to react under optimized conditions, in the presence of a bifunctional quinine-derived sterically encumbered squaramide (H-bond donor) organocatalyst. The conditions developed in this article have great advantages over the methods known in the literature in terms of reaction duration (1-6 h vs. 24-96 h) and reaction temperature (room temperature vs. -20 degrees C to -50 degrees C) giving rise to quite diastereoselective products with good enantioselectivities up to 97% ee.
dc.identifier.doi10.1039/d1nj05121k
dc.identifier.endpage606en_US
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue2en_US
dc.identifier.scopus2-s2.0-85122958964
dc.identifier.scopusqualityQ2
dc.identifier.startpage599en_US
dc.identifier.urihttps://hdl.handle.net/20.500.12846/642
dc.identifier.volume46en_US
dc.identifier.wosWOS:000728841400001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.institutionauthorGündoğdu, Gülsüm
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.relation.ispartofNew Journal Of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectAsymmetrıc 4+1 Cycloadditionsen_US
dc.subjectMichael Additionen_US
dc.subjectStereoselectıie Synthesisen_US
dc.subjectStereoseleksiyon Sentezien_US
dc.subjectStereoselektive Syntheseen_US
dc.subjectMichael Zusatzen_US
dc.subjectAsymmetrische 4+1 Cycloadditionenen_US
dc.titleEnantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst
dc.typeArticle

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