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Effect of 4-Hydroxy- -proline-containing podands on the stereoselectivity of Biginelli reaction according to molecular dynamicsстатья Исследовательская статья
Информация о цитировании статьи получена из
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 15 февраля 2024 г.
- Авторы: Borodina Olga, Ovchinnikova Irina, Fedorova Olga, Makarov Gennadiy, Bartashevich Ekaterina
- Журнал: Computational and theoretical chemistry
- Том: 1217
- Год издания: 2022
- Издательство: Elsevier
- Местоположение издательства: United States
- Номер статьи: 113885
- DOI: 10.1016/j.comptc.2022.113885
- Аннотация: The synthesis and theoretical study of the stereoselectivity of Biginelli reaction with chiral inductors based on 4-hydroxy-l-proline podands with four oxyethylene moieties have been performed. The predominant formation of the iminium intermediate during the interaction of the podand salt form with benzaldehyde was experimentally shown. Metadynamic simulation of reaction mixture with 4-hydroxy-l-proline-containing podand in salt and base forms allowed us to compare the probability of reactants approach from re- and Si-sides on the diffusion stage. We modeled the arrangement of reactants in the pre-reactional stage of alternative steps that could have a key effect on enantiomeric excess of 1,4-dihydropyrimidinone. Results showed that the interaction of a podand-acetoacetate adduct with N-benzylideneurea was preferred, when the podand was in a base form, while for a salt form, the intereaction with benzaldehyde was more favorable, which led to higher stereoselectivity. The effect of intermolecular interactions on the stabilization of prereaction states was analyzed.
- Добавил в систему: Макаров Геннадий Иванович