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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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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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Authors and Affiliations

  1. South Ural State University, 76 Lenina Ave., Chelyabinsk, 454080, Russia

    Olga S. Borodina, Gennady I. Makarov & Ekaterina V. Bartashevich

  2. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg, 620990, Russia

    Irina G. Ovchinnikova, Yulia A. Titova, Olga V. Fedorova, Gennady L. Rusinov & Valery N. Charushin

  3. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    Yulia A. Titova, Gennady L. Rusinov & Valery N. Charushin

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  1. Olga S. Borodina
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  2. Gennady I. Makarov
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  3. Ekaterina V. Bartashevich
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  4. Irina G. Ovchinnikova
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  5. Yulia A. Titova
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  6. Olga V. Fedorova
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  7. Gennady L. Rusinov
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  8. Valery N. Charushin
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Correspondence to Ekaterina V. Bartashevich.

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Dedicated to Academician O. N. Chupakhin on his birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(8), 755–761

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Borodina, O.S., Makarov, G.I., Bartashevich, E.V. et al. Theoretical conformational studies of podands containing (2S,4R)-4-hydroxyproline moieties. Chem Heterocycl Comp 55, 755–761 (2019). https://doi.org/10.1007/s10593-019-02531-4

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