Evaluation of the effect of iminium intermediates on the stereoselectivity of the Biginelli reaction involving hydroxyproline-containing podands.

Autor: Borodina, O. S., Bartashevich, E. V., Ovchinnikova, I. G., Fedorova, O. V., Rusinov, G. L.
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Zdroj: Russian Chemical Bulletin; Aug2023, Vol. 72 Issue 8, p1767-1780, 14p
Abstrakt: The results are presented of a theoretical study on assessment of the stereoselectivity of processes aimed at increasing the enantiomeric excess of chiral pyrimidinones, products of the Biginelli reaction. The effects of hydroxyproline-containing podands used as chiral inductors, viz., the influence of the base or salt forms and of the oxyethylene chain length in the stage of formation of iminium intermediates of the Biginelli reaction are considered. A methodology is proposed for modeling a multicomponent reaction mixture by the molecular dynamics method. The strategy proved itself in quantitative assessment of the stereoselectivity of the approach of urea molecule to the iminium stereoisomers under the conditions of a simulated diffusion stage of the reaction. The energy maps constructed in the polar coordinates make it possible to visually assess the preference of the reagent approach to the different diastereotopic sides. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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