Yayın: High diastereoselectivity induced by intermolecular hydrogen bonding in [3+2] cycloaddition reaction: experimental and computational mechanistic approaches
Tarih
Kurum Yazarları
Yıldırım, Ayhan
Yazarlar
Kaya, Yunus
Danışman
Dil
Türü
Yayıncı:
Wiley
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Özet
A 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.
Açıklama
Kaynak:
Anahtar Kelimeler:
Konusu
Chemistry, DFT, Diastereoselective synthesis, H-bonding, Maleimide, Nitrone, Transition states, Diels-alder reactions, 1,3-dipolar cycloaddition, Nitrone-cycloaddition, Dft, Complexes, (Z)-c,n-diphenylnitrone, Stereochemistry, Acids, Chemical bonds, Computation theory, Stereoselectivity, Cycloaddition, Density functional theory, Diastereoselective synthesis, H-bonding, Maleimides, Nitrones, Transition state, Hydrogen bonds
Alıntı
Yıldırım, 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).