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Stereoselective synthesis of dihydropyrimidinethione podand in the presence of l-proline or 4-hydroxy-l-proline and metal nitrates

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Abstract

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.

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoy, 620108, Ekaterinburg, Russia

    E. S. Filatova, O. V. Fedorova, I. G. Ovchinnikova, K. A. Chistyakov, G. L. Rusinov & V. N. Charushin

  2. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Ekaterinburg, Russia

    G. L. Rusinov & V. N. Charushin

Authors
  1. E. S. Filatova
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  2. O. V. Fedorova
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  3. I. G. Ovchinnikova
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  4. K. A. Chistyakov
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  5. G. L. Rusinov
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  6. V. N. Charushin
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Corresponding author

Correspondence to E. S. Filatova.

Additional information

Dedicated to Academician of the Russian Academy of Sciences V. I. Ovcharenko on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1506–1513, July, 2022.

This work was carried out in terms of state assignments AAAA-A19-119012290117-6 and AAAA-A19-119012490007-8 using equipment of the Center for Collective Use “Spectroscopy and Analysis of Organic Compounds.”

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Filatova, E.S., Fedorova, O.V., Ovchinnikova, I.G. et al. Stereoselective synthesis of dihydropyrimidinethione podand in the presence of l-proline or 4-hydroxy-l-proline and metal nitrates. Russ Chem Bull 71, 1506–1513 (2022). https://doi.org/10.1007/s11172-022-3557-4

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  • DOI: https://doi.org/10.1007/s11172-022-3557-4

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