Kaya, Yunus2023-09-052023-09-052017-06-01Yıldırım, 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).0894-32301099-1395https://doi.org/10.1002/poc.3629https://onlinelibrary.wiley.com/doi/10.1002/poc.3629http://hdl.handle.net/11452/33740A 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.eninfo:eu-repo/semantics/closedAccessChemistryDFTDiastereoselective synthesisH-bondingMaleimideNitroneTransition statesDiels-alder reactions1,3-dipolar cycloadditionNitrone-cycloadditionDftComplexes(Z)-c,n-diphenylnitroneStereochemistryAcidsChemical bondsComputation theoryStereoselectivityCycloadditionDensity functional theoryDiastereoselective synthesisH-bondingMaleimidesNitronesTransition stateHydrogen bondsArticle0004044482000012-s2.0-85019198551306Chemistry, organicChemistry, physicalNitrones; Cycloaddition Reactions; Isoxazole Derivative