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Synthesis of optically active omeprazole by catalysis with vanadyl complexes with chiral Schiff bases

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Abstract

A new method for the preparation of optically active omeprazole, consisting in asymmetric oxidation of the corresponding sulfide with the use of vanadyl complexes with chiral Schiff bases as the catalysts has been elaborated. The best results of the oxidation were achieved by the use of the combination VO(acac)2—2-[{(1S,2S,3R,5S)-3-hydroxymethyl-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-ylimino}methyl]phenol—N-ethyl-N,N-diisopropylamine.

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Authors and Affiliations

  1. Novosibirsk State University, 2 ul. Pirogova, 630090, Novosibirsk, Russian Federation

    E. A. Koneva

  2. N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    T. M. Khomenko, S. Yu. Kurbakova, N. I. Komarova, D. V. Korchagina, K. P. Volcho, N. F. Salakhutdinov & G. A. Tolstikov

  3. G. K. Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 5 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    A. G. Tolstikov

Authors
  1. E. A. Koneva
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  2. T. M. Khomenko
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  3. S. Yu. Kurbakova
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  4. N. I. Komarova
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  5. D. V. Korchagina
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  6. K. P. Volcho
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  7. N. F. Salakhutdinov
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  8. A. G. Tolstikov
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  9. G. A. Tolstikov
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Corresponding author

Correspondence to K. P. Volcho.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1648–1653, August, 2008.

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Koneva, E.A., Khomenko, T.M., Kurbakova, S.Y. et al. Synthesis of optically active omeprazole by catalysis with vanadyl complexes with chiral Schiff bases. Russ Chem Bull 57, 1680–1685 (2008). https://doi.org/10.1007/s11172-008-0221-6

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  • DOI: https://doi.org/10.1007/s11172-008-0221-6

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