Catalysis Letters

, Volume 146, Issue 2, pp 493–498 | Cite as

Asymmetric Biginelli Reaction Catalyzed by Silicon, Titanium and Aluminum Oxides

  • Olga V. Fedorova
  • Yulia A. TitovaEmail author
  • Alexey Yu. Vigorov
  • Maria S. Toporova
  • Olga A. Alisienok
  • Anna N. Murashkevich
  • Victor P. Krasnov
  • Gennady L. Rusinov
  • Valery N. Charushin


The asymmetric Biginelli reaction was investigated in the presence of N-[(2S,4R)-4-hydroxyprolyl]-(S)-1-phenylethylamine as chiral inducer and silicon, titanium or aluminum oxides (individual and mixed, bulk and nanosized) as heterogeneous catalysts. It has been shown that all studied oxides improve chemo- and stereoselectivity of the Biginelli reaction.

Graphical Abstract


Asymmetric catalysis The Biginelli reaction Condensation Nanoparticles Chemoselectivity Heterogeneous catalysis 



This study was financially supported by the Russian Foundation for Basic Research (Projects Nos. 13-03-12188-ofi_m and 14-03-31357-mol_a).


  1. 1.
    Kappe CO (1993) Tetrahedron 49:6937CrossRefGoogle Scholar
  2. 2.
    Vdovina SV, Mamedov VA (2008) Russ Chem Rev 77:1017CrossRefGoogle Scholar
  3. 3.
    Sandhu SS, Sandhu JS (2012) ARKIVOC i:66Google Scholar
  4. 4.
    Heravi MM, Asadi S, Lashkariani BM (2013) Mol Divers 17:389CrossRefGoogle Scholar
  5. 5.
    Wan JP, Lina Y, Liua Y (2014) Curr Org Chem 18:687CrossRefGoogle Scholar
  6. 6.
    Graaff C, Ruijter E, Orru RVA (2012) Chem Soc Rev 41:3969CrossRefGoogle Scholar
  7. 7.
    Wang M, Xie MH, Wu CD, Wang YG (2009) Chem Commun 17:2396CrossRefGoogle Scholar
  8. 8.
    Titova Y, Fedorova O, Rusinov G, Vigorov A, Krasnov V, Murashkevich A, Charushin V (2015) Catal Today 241:270CrossRefGoogle Scholar
  9. 9.
    Uhm YR, Lee HM, Fedorova O, Ovchinnikova I, Valova M, Rusinov G, Charushin V, Rhee CK (2010) Res Chem Intermed 36:867CrossRefGoogle Scholar
  10. 10.
    Fedorova OV, Valova MS, Yua T, Ovchinnikova IG, Grishakov AN, Uimin MA, Mysik AA, Ermakov AE, Rusinov GL, Charushin VN (2011) Kinet Catal 52:226CrossRefGoogle Scholar
  11. 11.
    Krivtsov IV, Titova YuA, Ilkaeva MV, Avdin VV, Fedorova OV, Khainakov SA, Garcia JR, Rusinov GL, Charushin VN (2014) J Sol-Gel. Sci Technol 69:448Google Scholar
  12. 12.
    Xin J, Chang L, Hou Z, Shang D, Liu X, Feng X (2008) Chem Eur J 14:3177CrossRefGoogle Scholar
  13. 13.
    Davydov A (2003) Molecular spectroscopy of oxide catalyst surfaces. Wiley-Ltd, ChichesterCrossRefGoogle Scholar
  14. 14.
    Kleidernigg OP, Kappe CO (1997) Tetrahedron Asymmetry 8:2057CrossRefGoogle Scholar
  15. 15.
    Syed NA, Muhammad MH (2011) J Chromatogr Sci 49:292CrossRefGoogle Scholar
  16. 16.
    Murashkevich AN, Alisienok OA, Zharskiy IM, Yukhno EK (2013) J Sol-Gel Sci Technol 68:509CrossRefGoogle Scholar
  17. 17.
    Murashkevich AN, Lavitskaya AS, Barannikova TI, Zharskii IM (2008) J Appl Spectrosc 75:730CrossRefGoogle Scholar
  18. 18.
    Fedorova OV, Koryakova OV, Valova MS, Ovchinnikova IG, Titova YA, Rusinov GL, Charushin VN (2010) Kinet Catal 51:566CrossRefGoogle Scholar
  19. 19.
    Liberto NA, Silva SP, Fátima ÂD, Fernandes SA (2013) Tetrahedron 69:8245CrossRefGoogle Scholar
  20. 20.
    Valova MS, Koryakova OV, Maximovskikh AI, Fedorova OV, Murashkevich AN, Alisienok OA (2014) J Appl Spectrosc 81:422CrossRefGoogle Scholar
  21. 21.
    Tanabe K (1970) Solid acids and bases. Their catalytic properties. Academic Press, New-YorkGoogle Scholar
  22. 22.
    Alvim HGO, Silva EN, Neto BAD (2014) RSC Adv 4:54282CrossRefGoogle Scholar
  23. 23.
    Puripat M, Ramozzi R, Hatanaka M, Parasuk W, Parasuk V, Morokuma K (2015) J Org Chem 80:6959CrossRefGoogle Scholar
  24. 24.
    An D, Fan YS, Gao Y, Zhu ZQ, Zheng LY, Zhang SQ (2014) Eur J Org Chem 2:301CrossRefGoogle Scholar
  25. 25.
    Kappe CO (1997) J Org Chem 62:7201CrossRefGoogle Scholar
  26. 26.
    De Souza ROMA, Da Penha ET, Milagre HMS, Garden SJ, Esteves PM, Eberlin MN, Antunes OAC (2009) Chem Eur J 15:9799CrossRefGoogle Scholar
  27. 27.
    Titova YuA, Fedorova OV, Rusinov GL, Charushin VN (2015) Russ Chem Rev 84:1294CrossRefGoogle Scholar
  28. 28.
    Saha S, Moorthy JN (2011) J Org Chem 76:396CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Olga V. Fedorova
    • 1
    • 3
  • Yulia A. Titova
    • 1
    • 3
    Email author
  • Alexey Yu. Vigorov
    • 1
  • Maria S. Toporova
    • 1
  • Olga A. Alisienok
    • 2
  • Anna N. Murashkevich
    • 2
  • Victor P. Krasnov
    • 1
  • Gennady L. Rusinov
    • 1
    • 3
  • Valery N. Charushin
    • 1
    • 3
  1. 1.Postovsky Institute of Organic Synthesis, Ural BranchRussian Academy of SciencesYekaterinburgRussia
  2. 2.Belarusian State Technical UniversityMinskBelarus
  3. 3.Ural Federal University Named after the First President of Russia B.N. YeltsinYekaterinburgRussia

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