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

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dc.contributor.authorKaya, Yunus
dc.contributor.buuauthorYıldırım, Ayhan
dc.contributor.departmentFen Edebiyat Fakültesi
dc.contributor.departmentKimya Bölümü
dc.contributor.orcid0000-0002-2328-9754
dc.contributor.researcheridW-8924-2019
dc.contributor.scopusid23101773900
dc.date.accessioned2023-09-05T05:53:24Z
dc.date.available2023-09-05T05:53:24Z
dc.date.issued2017-06-01
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.
dc.identifier.citationYıldırım, A. ve Kaya, Y. (2017). ''High diastereoselectivity induced by intermolecular hydrogen bonding in [3+2] cycloaddition reaction: experimental and computational mechanistic approaches''. Journal of Physical Organic Chemistry, 30(6).
dc.identifier.issn0894-3230
dc.identifier.issn1099-1395
dc.identifier.issue6
dc.identifier.scopus2-s2.0-85019198551
dc.identifier.urihttps://doi.org/10.1002/poc.3629
dc.identifier.urihttps://onlinelibrary.wiley.com/doi/10.1002/poc.3629
dc.identifier.urihttp://hdl.handle.net/11452/33740
dc.identifier.volume30
dc.identifier.wos000404448200001
dc.indexed.wosSCIE
dc.language.isoen
dc.publisherWiley
dc.relation.collaborationYurt içi
dc.relation.journalJournal of Physical Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectChemistry
dc.subjectDFT
dc.subjectDiastereoselective synthesis
dc.subjectH-bonding
dc.subjectMaleimide
dc.subjectNitrone
dc.subjectTransition states
dc.subjectDiels-alder reactions
dc.subject1,3-dipolar cycloaddition
dc.subjectNitrone-cycloaddition
dc.subjectDft
dc.subjectComplexes
dc.subject(Z)-c,n-diphenylnitrone
dc.subjectStereochemistry
dc.subjectAcids
dc.subjectChemical bonds
dc.subjectComputation theory
dc.subjectStereoselectivity
dc.subjectCycloaddition
dc.subjectDensity functional theory
dc.subjectDiastereoselective synthesis
dc.subjectH-bonding
dc.subjectMaleimides
dc.subjectNitrones
dc.subjectTransition state
dc.subjectHydrogen bonds
dc.subject.scopusNitrones; Cycloaddition Reactions; Isoxazole Derivative
dc.subject.wosChemistry, organic
dc.subject.wosChemistry, physical
dc.titleHigh diastereoselectivity induced by intermolecular hydrogen bonding in [3+2] cycloaddition reaction: experimental and computational mechanistic approaches
dc.typeArticle
dc.wos.quartileQ3
dspace.entity.typePublication
local.contributor.departmentFen Edebiyat Fakültesi/Kimya Bölümü
local.indexed.atScopus
local.indexed.atWOS

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