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High diastereoselectivity induced by intermolecular hydrogen bonding in [3 + 2] cycloaddition reaction: experimental and computational mechanistic approaches
Author(s) -
Yıldırım Ayhan,
Kaya Yunus
Publication year - 2017
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3629
Subject(s) - cycloaddition , chemistry , intermolecular force , steric effects , diastereomer , nitrone , substituent , hydrogen bond , density functional theory , computational chemistry , yield (engineering) , transition state , medicinal chemistry , stereochemistry , organic chemistry , molecule , catalysis , materials science , metallurgy
A diastereoselective [3 + 2] cycloaddition of N ‐aryl substituted maleimides with N , α ‐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.