High diastereoselectivity induced by intermolecular hydrogen bonding in [3+2] cycloaddition reaction: experimental and computational mechanistic approaches
Küçük Resim Yok
Tarih
2017
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Wiley
Erişim Hakkı
info:eu-repo/semantics/closedAccess
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
Anahtar Kelimeler
DFT, diastereoselective synthesis, H-bonding, maleimide, nitrone, transition states
Kaynak
Journal Of Physical Organic Chemistry
WoS Q Değeri
Q3
Scopus Q Değeri
Q3
Cilt
30
Sayı
6
