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New chiral proline-based catalysts for silicon and zirconium oxides-promoted asymmetric Biginelli reaction

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Chemistry of Heterocyclic Compounds Aims and scope

4-Hydroxy-(2S)-prolines bearing 3,4-dihydro-2H-1,4-benzoxazine or 1,2,3,4-tetrahydroquinoline fragments were synthesized and studied as chiral catalysts in the Biginelli reaction. The target product ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate was obtained with 54% enantiomeric excess (ee). An increase in ee values of the reaction product up to 76% was observed in the presence of nanosized oxides SiO2–ZrO2 as heterogeneous promoters.

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Authors and Affiliations

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

    Yulia A. Titova, Dmitry A. Gruzdev, Olga V. Fedorova, Victor P. Krasnov, Gennady L. Rusinov & Valery N. Charushin

  2. Belarusian State Technical University, 13a Sverdlova St., 220006, Minsk, Belarus

    Olga A. Alisienok & Anna N. Murashkevich

  3. Ural Federal University named after the First President of Russia B. N. Yeltsin, 28 Mira St., Yekaterinburg, 620002, Russia

    Gennady L. Rusinov & Valery N. Charushin

Authors
  1. Yulia A. Titova
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  2. Dmitry A. Gruzdev
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  3. Olga V. Fedorova
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  4. Olga A. Alisienok
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  5. Anna N. Murashkevich
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  6. Victor P. Krasnov
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  7. Gennady L. Rusinov
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  8. Valery N. Charushin
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Correspondence to Yulia A. Titova.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(4), 417–427

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Titova, Y.A., Gruzdev, D.A., Fedorova, O.V. et al. New chiral proline-based catalysts for silicon and zirconium oxides-promoted asymmetric Biginelli reaction. Chem Heterocycl Comp 54, 417–427 (2018). https://doi.org/10.1007/s10593-018-2285-z

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  • DOI: https://doi.org/10.1007/s10593-018-2285-z

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