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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 8, pp 755–761 | Cite as

Theoretical conformational studies of podands containing (2S,4R)-4-hydroxyproline moieties

  • Olga S. Borodina
  • Gennady I. Makarov
  • Ekaterina V. BartashevichEmail author
  • Irina G. Ovchinnikova
  • Yulia A. Titova
  • Olga V. Fedorova
  • Gennady L. Rusinov
  • Valery N. Charushin
Article
  • 14 Downloads

Podands derived from (2S,4R)-4-hydroxyproline and containing two oxygen atoms in the oxyethylene moiety were selected for computational studies of their conformational behavior in solutions and further theoretical studies of their role as chiral inductors of Biginelli reaction. Qualitative differences were identified between the conformations of the basic podand and its bis(trifluoroacetate) derivative. Molecular dynamics simulations and quantum-chemical calculations showed that the bicationic form of podand, in contrast to the corresponding basic one, featured an intramolecular hydrogen bond between the 4-hydroxyproline moieties of terminal groups, which led to a noticeable increase in the averaged rotational energy barriers and a greater energy difference between the predominant conformer structures. The subsequent theoretical evaluation of chemical shifts for the various conformers and comparison of the observed values with experimentally obtained 1Н NMR data allowed to confirm the differences between the conformational behavior of (2S,4R)-4-hydroxyproline podand and its bicationic salt in stereoselective Biginelli reactions.

Keywords

(2S,4R)-4-hydroxyproline podand chemical shift chiral inductor conformational analysis GIAO method 1Н NMR spectroscopy 

Notes

This work was performed with financial support provided by State assignment No. 075005781900 of the Ministry of Education and Science of the Russian Federation, with partial support from the Russian Foundation for Basic Research (project 16-29-10757-ofi_m), as well as with support from the Ministry of Science and Higher Education of the Russian Federation (project 4.1157.2017/4.6, action 211, contract 02.A03.21.0011).

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Olga S. Borodina
    • 1
  • Gennady I. Makarov
    • 1
  • Ekaterina V. Bartashevich
    • 1
    Email author
  • Irina G. Ovchinnikova
    • 2
  • Yulia A. Titova
    • 2
    • 3
  • Olga V. Fedorova
    • 2
  • Gennady L. Rusinov
    • 2
    • 3
  • Valery N. Charushin
    • 2
    • 3
  1. 1.South Ural State UniversityChelyabinskRussia
  2. 2.Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesYekaterinburgRussia
  3. 3.Ural Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia

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