NEW CHIRAL PROLINE-BASED CATALYSTS FOR SILICON AND ZIRCONIUM OXIDES-PROMOTED ASYMMETRIC BIGINELLI REACTION

Authors

  • Yulia Titova Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch)
  • Dmitry Gruzdev Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch)
  • Olga Fedorova Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch)
  • Olga Alisienok Belarusian State Technical University
  • Anna Murashkevich Belarusian State Technical University
  • Victor Krasnov Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch)
  • Gennady Rusinov Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch); Ural Federal University named after the First President of Russia B.N. Yeltsin
  • Valery Charushin Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch); Ural Federal University named after the First President of Russia B.N. Yeltsin

DOI:

https://doi.org/10.1007/4339

Keywords:

hydroxyproline, silica oxide, zirconium oxide, asymmetric catalysis, Biginelli reaction, nanosized oxide.

Abstract

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.

Author Biography

Yulia Titova, Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch)

н.с. лаборатории гетероциклических соединений

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Published

2018-06-04

Issue

Vol. 54 No. 4 (2018): Stereoselective synthesis of heterocyclic compounds

Section

Original Papers