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Conjugates of Bispidine and Monoterpenoids as Ligands of Metal Complex Catalysts for the Henry Reaction

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Abstract

A number of chiral chelating conjugates combining a bispidine central backbone and one or two pinene side fragments were synthesized. It was shown for the first time that the synthesized compounds are capable to act as catalysts in the Henry reaction both individually and in the presence of metal salts. It was found that the best catalytic results were shown for bis-tertiary amine combining bispidinone and two (–)-myrtenol fragments, and copper as well as zinc acetates.

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ACKNOWLEDGMENTS

The authors are grateful to the Chemical Research Center for Collective Use, Siberian Branch, Russian Academy of Sciences, for spectral and analytical measurements. The mass spectra were measured using the equipment of the Center for Collective Use, Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences.

Funding

The work was financially supported by the Russian Science Foundation (project no. 19-73-20090).

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Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    E. S. Mozhaitsev, K. Y. Ponomarev, O. S. Patrusheva, A. D. Rogachev, N. I. Komarova, D. V. Korchagina, E. V. Suslov, K. P. Volcho & N. F. Salakhutdinov

  2. Lomonosov Moscow State University, 119991, Moscow, Russia

    A. V. Medvedko, A. I. Dalinger & S. Z. Vatsadze

Authors
  1. E. S. Mozhaitsev
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  2. K. Y. Ponomarev
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  3. O. S. Patrusheva
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  4. A. V. Medvedko
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  5. A. I. Dalinger
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  6. A. D. Rogachev
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  7. N. I. Komarova
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  8. D. V. Korchagina
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  9. E. V. Suslov
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  10. K. P. Volcho
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  11. N. F. Salakhutdinov
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  12. S. Z. Vatsadze
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Correspondence to S. Z. Vatsadze.

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Mozhaitsev, E.S., Ponomarev, K.Y., Patrusheva, O.S. et al. Conjugates of Bispidine and Monoterpenoids as Ligands of Metal Complex Catalysts for the Henry Reaction. Russ J Org Chem 56, 1969–1981 (2020). https://doi.org/10.1134/S1070428020110123

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  • DOI: https://doi.org/10.1134/S1070428020110123

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