СТЕРЕОСЕЛЕКТИВНЫЙ СИНТЕЗ ДИГИДРОПИРИМИДИНТИОНОВОГО ПОДАНДА В ПРИСУТСТВИИ L-ПРОЛИНА ИЛИ 4-ГИДРОКСИ-L-ПРОЛИНА И НИТРАТОВ МЕТАЛЛОВ

科研成果: Article同行评审

摘要

The asymmetric Biginelli reaction involving a 3-oxobutanoyl-containing podand, benzaldehyde, and thiourea was studied using secondary amines as a chiral inductor, Brönsted acid as a catalyst, and metal salts (especially metal nitrates) as an additive of asymmetric catalysis (AAC) was studied. The tuberculostatically active dihydropyrimidine-thione-containing podand was synthesized with an enantiomeric excess of 57% in the presence of 4-hydroxy-L-proline. In the presence of metal nitrates, the influence of the ionic radius of the cation on the enantioselective excess of the reaction under study was observed, which made it possible to propose a possible mechanism of chiral induction controlled by the complexing ability of the initial β-ketoester-containing podand with metal ions and coordination of the reagents in the transition states.
投稿的翻译标题STEREOSELECTIVE SYNTHESIS OF DIHYDROPYRIMIDINETHIONE PODAND IN THE PRESENCE OF L-PROLINE OR 4-HYDROXY-L-PROLINE AND METAL NITRATES
源语言Russian
页(从-至)1506-1513
页数8
期刊Известия Академии наук. Серия химическая
7
Published - 2022

GRNTI

  • 31.00.00 CHEMISTRY

Level of Research Output

  • VAK List
  • Russian Science Citation Index

指纹

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