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

Yildirim, AyhanKaya, Yunus2021-03-202021-03-2020170894-32301099-1395http://doi.org/10.1002/poc.3629https://hdl.handle.net/20.500.12885/948A 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/closedAccessDFTdiastereoselective synthesisH-bondingmaleimidenitronetransition statesHigh diastereoselectivity induced by intermolecular hydrogen bonding in [3+2] cycloaddition reaction: experimental and computational mechanistic approachesArticle10.1002/poc.3629306WOS:000404448200001Q3Q3