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Başlık: High diastereoselectivity induced by intermolecular hydrogen bonding in [3+2] cycloaddition reaction: experimental and computational mechanistic approaches
Yazarlar: Kaya, Yunus
Uludağ Üniversitesi/Fen-Edebiyat Fakültesi/Kimya Bölümü.
0000-0002-2328-9754
Yıldırım, Ayhan
W-8924-2019
23101773900
Anahtar kelimeler: 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
Yayın Tarihi: 1-Haz-2017
Yayıncı: Wiley
Atıf: 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).
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.
URI: https://doi.org/10.1002/poc.3629
https://onlinelibrary.wiley.com/doi/10.1002/poc.3629
http://hdl.handle.net/11452/33740
ISSN: 0894-3230
1099-1395
Koleksiyonlarda Görünür:Scopus
Web of Science

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