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New chiral Schiff bases derived from (+)- and (−)-α-pinenes in the metal complex catalyzed asymmetric oxidation of sulfides

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Abstract

New chiral Schiff bases were derived from (+)- and (−)-α-pinenes for the first time. Coordinated to vanadium ions, they can be used as ligands in catalytic oxidation of sulfides into chiral sulfoxides. Conditions for the asymmetric oxidation of thioanisole to methyl phenyl sulfoxide in optical purity up to 32% were found. Variation of substituents in the ligand has a significant effect not only on enantioselectivity of the reaction, but also on absolute configuration of the sulfoxide formed.

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

    K. P. Volcho, D. V. Korchagina, N. I. Komarova, A. I. Kochnev & N. F. Salakhutdinov

  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. K. P. Volcho
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  3. D. V. Korchagina
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  4. N. I. Komarova
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  5. A. I. Kochnev
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  6. N. F. Salakhutdinov
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  7. A. G. Tolstikov
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Corresponding author

Correspondence to K. P. Volcho.

Additional information

Dedicated to Academician G. A. Tolstikov in honor of his 75th anniversary.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 105–113, January, 2008.

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Koneva, E.A., Volcho, K.P., Korchagina, D.V. et al. New chiral Schiff bases derived from (+)- and (−)-α-pinenes in the metal complex catalyzed asymmetric oxidation of sulfides. Russ Chem Bull 57, 108–117 (2008). https://doi.org/10.1007/s11172-008-0017-8

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  • DOI: https://doi.org/10.1007/s11172-008-0017-8

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