Abstract:
The enantioselectivity of the Diels–Alder reaction between (E)-3-(4-nitrophenyl)-1-(pyridin-3-yl)prop-2-en-1-one and cyclopenta-1,3-diene in the chiral ionic liquids 3-butyl-1-methylimidazolium (S)-camphorsulfonate and (S)-1-methyl-3-(pyrrolidin-2-ylmethyl)- imidazolium tosylate or upon chiral promotion with chiral oxazaborolidine was modeled by molecular and quantum mechanics and then experimentally studied; computations were in good agreement with the experimental data, resulting in no stereoselectivity with a chiral ionic liquid used as a co-solvent and prominent stereoselectivity upon chiral promotion.
Document Type:
Article
Language: English
Citation:
A. A. Zeifman, V. S. Stroylov, I. Yu. Titov, F. N. Novikov, O. V. Stroganov, I. Svitanko, G. G. Chilov, “Modeling of the Diels–Alder reaction enantioselectivity by quantum mechanics and molecular mechanics”, Mendeleev Commun., 25:4 (2015), 269–270
Linking options:
https://www.mathnet.ru/eng/mendc2376
https://www.mathnet.ru/eng/mendc/v25/i4/p269
This publication is cited in the following 5 articles:
I. V. Svitanko, T. S. Pivina, “Molecular modeling in synthesis: from statistical methods to quantum chemistry and practical applications”, Russ Chem Bull, 73:5 (2024), 1093
I. Yu. Titov, V. S. Stroylov, P. V. Rusina, I. Svitanko, “Preliminary modelling as the first stage of targeted organic synthesis”, Russian Chem. Reviews, 90:7 (2021), 831–867
Qin Wu, Quan Shi, Jiqing Shang, Min Wang, Hansheng Li, Daxin Shi, Yun Zhao, Qingze Jiao, “Synthesis of Surface-Active Heteropolyacid-Based Ionic Liquids and Their Catalytic Performance for Desulfurization of Fuel Oils”, ACS Omega, 5:48 (2020), 31171
I. V. Mikhura, A. A. Formanovsky, E. V. Nozhevnikova, I. A. Prokhorenko, V. A. Korshun, “Dianhydrides of 1(4)-substituted 7,8-diphenylbicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic acids”, Mendeleev Commun., 27:5 (2017), 446–447
Jiahan Sun, Hansheng Li, Haoran Song, Qin Wu, Yun Zhao, Qingze Jiao, “Synthesis of methylal from methanol and formaldehyde catalyzed by Brønsted acid ionic liquids with different alkyl groups”, RSC Adv., 5:106 (2015), 87200
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