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Terpene ligands as the basis of catalytic systems for the asymmetric oxidation of phenylphenacyl sulfide

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Abstract

Terpene ligands (1S,2S,5S)-3-[{2-[(2-hydroxybenzylidene)amino]ethyl}imino]-2,6,6-trimethylbicyclo[3.1.1.]heptane-2-ol and 3-({2-[(2-hydroxy-2,6,6-trimethylbicyclo[3.1.1.]hept-3-ilidene)amino]ethyl}imino)-2,6,6-trimethylbicyclo[3.1.1.]heptane-2-ol have been synthesized for the first time. The efficiency of complexes based on terpene and salen ligands in asymmetric sulfoxidation has been compared. Catalytic systems based on terpene ligands have been used for the first time in the asymmetric oxidation of phenylphenacyl sulfide with the formation of sulfoxide with an enantiomeric excess of 47%.

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Abbreviations

CHP:

cumyl hydroperoxide

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Authors and Affiliations

  1. Institute of Chemistry, Komi Research Center, Ural Division, Russian Academy of Sciences, ul. Pervomaiskaya 48, Syktyvkar, 167982, Russia

    A. V. Kuchin, E. V. Ashikhmina, S. A. Rubtsova & I. A. Dvornikova

Authors
  1. A. V. Kuchin
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  2. E. V. Ashikhmina
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  3. S. A. Rubtsova
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  4. I. A. Dvornikova
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Correspondence to E. V. Ashikhmina.

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Original Russian Text © A.V. Kuchin, E.V. Ashikhmina, S.A. Rubtsova, I.A. Dvornikova, 2010, published in Khimiya Rastitel’nogo Syr’ya, 2009, No. 1, pp. 59–66.

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Kuchin, A.V., Ashikhmina, E.V., Rubtsova, S.A. et al. Terpene ligands as the basis of catalytic systems for the asymmetric oxidation of phenylphenacyl sulfide. Russ J Bioorg Chem 36, 877–883 (2010). https://doi.org/10.1134/S1068162010070150

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