High diastereoselectivity induced by intermolecular hydrogen bonding in [3+2] cycloaddition reaction: experimental and computational mechanistic approaches

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dc.authorid0000-0001-7228-2340en_US
dc.contributor.authorYildirim, Ayhan
dc.contributor.authorKaya, Yunus
dc.date.accessioned2021-03-20T20:13:50Z
dc.date.available2021-03-20T20:13:50Z
dc.date.issued2017
dc.departmentBTÜ, Mühendislik ve Doğa Bilimleri Fakültesi, Kimya Bölümüen_US
dc.description.abstractA diastereoselective [3 + 2] cycloaddition of N-aryl substituted maleimides with N, a-diphenyl nitrone possessing 11-hydroxyundecyloxy as a flexible substituent was performed. Experimental and comprehensive mechanistic density functional theory studies reveals that intermolecular H-bonding and steric repulsive interaction predominate exo-Z and exo-E cycloaddition transition states, respectively. The reaction proceeded smoothly depending on the reactants and gave a good yield of (syn) cis-isoxazolidine or (anti) trans-isoxazolidine as a single diastereomer.en_US
dc.identifier.doi10.1002/poc.3629en_US
dc.identifier.issn0894-3230
dc.identifier.issn1099-1395
dc.identifier.issue6en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.urihttp://doi.org/10.1002/poc.3629
dc.identifier.urihttps://hdl.handle.net/20.500.12885/948
dc.identifier.volume30en_US
dc.identifier.wosWOS:000404448200001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.institutionauthorKaya, Yunus
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.ispartofJournal Of Physical Organic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectDFTen_US
dc.subjectdiastereoselective synthesisen_US
dc.subjectH-bondingen_US
dc.subjectmaleimideen_US
dc.subjectnitroneen_US
dc.subjecttransition statesen_US
dc.titleHigh diastereoselectivity induced by intermolecular hydrogen bonding in [3+2] cycloaddition reaction: experimental and computational mechanistic approachesen_US
dc.typeArticleen_US

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