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Catalysts for enantioselective Biginelli reaction based on the composite silica-zirconia xerogels prepared using different zirconium sources

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Abstract

The composite silica-zirconia xerogels have been prepared via sol–gel method using zirconium oxychloride, oxynitrate, acetate and sodium silicate as the precursors. The prepared materials have been characterized using FTIR, TG/DTA, EDX and surface area analyses. It has been established that surface area of silica-zirconia xerogels significantly depends on the zirconium source, but phase transitions and structural features of the xerogels seem to be unaffected by the choice of the zirconia precursor. Prepared xerogels increase the activity of chiral inductor in the asymmetric Biginelli reaction. The anion of the zirconium salt adsorbed on the surface of the synthesized material and the presence of Si–O–Zr heterolinkages determines the reaction yield. The highest chemo- and enantioselectivity towards formation of ee isomer have been provided by the catalyst prepared from zirconium oxychloride.

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Acknowledgments

The study is carried out within the grant of Russian Ministry of Education No. 01201255647. This work was supported by the Russian Foundation for Basic Research, 12-03-90039-Bel_a, 13-03-12188-ofi_m, 14-03-31357 mol_a; by the Ural Branch, Russian Academy of Sciences, project nos. 12-P-234-2003 and 12-P-3-1030; and by the State Program for the Support of Leading Scientific Schools, Grant NSh 5505.2012.3.

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Authors and Affiliations

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

    I. V. Krivtsov, M. V. Ilkaeva & V. V. Avdin

  2. I.Ya. Postovsky Institute of Organic Synthesis of RAS, Urals Branch, S. Kovalevskoy Str. 22, Ekaterinburg, Russia

    Yu. A. Titova, O. V. Fedorova, G. L. Rusinov & V. N. Charushin

  3. University of Oviedo, Julian Claveria 8, 33006, Oviedo, Spain

    S. A. Khainakov & J. R. Garcia

Authors
  1. I. V. Krivtsov
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  2. Yu. A. Titova
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  3. M. V. Ilkaeva
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  4. V. V. Avdin
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  5. O. V. Fedorova
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  6. S. A. Khainakov
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  7. J. R. Garcia
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  8. G. L. Rusinov
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  9. V. N. Charushin
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Correspondence to I. V. Krivtsov.

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Krivtsov, I.V., Titova, Y.A., Ilkaeva, M.V. et al. Catalysts for enantioselective Biginelli reaction based on the composite silica-zirconia xerogels prepared using different zirconium sources. J Sol-Gel Sci Technol 69, 448–452 (2014). https://doi.org/10.1007/s10971-013-3242-z

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  • DOI: https://doi.org/10.1007/s10971-013-3242-z

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