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Synthesis of (4Z)-Unsaturated Iodo-δ-lactones by Catalytic Cross-Cyclomagnesiation

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Abstract

6-[(4Z)-1-Iodoalk-4-en-1-yl]tetrahydropyran-2-ones (iodo-δ-lactone analogs) were synthesized for the first time from 5Z,9Z-alka-5,9-dienoic acids in three steps through Cp2TiCl2-catalyzed intermolecular cyclo­magnesiation of aliphatic and oxygen-containing 1,2-dienes in the key step.

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ACKNOWLEDGMENTS

The spectral studies were performed at the Agidel regional joint center, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

This study was financially supported in the framework of state assignment.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 450075, Ufa, Russia

    A. A. Makarov, I. V. Ishbulatov & E. Kh. Makarova

  2. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    V. A. D’yakonov & U. M. Dzhemilev

Authors
  1. A. A. Makarov
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  2. I. V. Ishbulatov
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  3. E. Kh. Makarova
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  4. V. A. D’yakonov
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  5. U. M. Dzhemilev
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Correspondence to A. A. Makarov.

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Makarov, A.A., Ishbulatov, I.V., Makarova, E.K. et al. Synthesis of (4Z)-Unsaturated Iodo-δ-lactones by Catalytic Cross-Cyclomagnesiation. Russ J Org Chem 58, 1954–1958 (2022). https://doi.org/10.1134/S1070428022120259

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  • DOI: https://doi.org/10.1134/S1070428022120259

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