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Nucleophilic addition to acetylenes in superbasic catalytic systems. 12. Vinylation of lupinine

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Abstract

The addition of a natural alkaloid lupinine to acetylene in the presence of superbasic catalytic systems (KOH—DMSO, KOBut—DMSO, KOH—dioxane) under elevated or atmospheric pressure affords O-vinyllupinine (in up to 88% yield), a promising optically active monomer and intermediate for the preparation of new quinolizidine alkaloids. The same vinyl ether was obtained (in 60% yield) by the reaction of lupinine with vinyl acetate in the presence of Hg(OAc)2.

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 ul. Favorskogo, 664033, Irkutsk, Russian Federation

    L. A. Oparina, T. G. Ermakova, N. P. Kuznetsova, L. V. Kanitskaya, A. P. Tantsyrev & B. A. Trofimov

  2. Karakalpakstan State University, 1 ul. Universitetskaya, 742012, Nukus, Uzbekistan

    R. T. Tlegenov

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  1. L. A. Oparina
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  2. R. T. Tlegenov
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  3. T. G. Ermakova
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  4. N. P. Kuznetsova
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  5. L. V. Kanitskaya
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  6. A. P. Tantsyrev
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  7. B. A. Trofimov
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Oparina, L.A., Tlegenov, R.T., Ermakova, T.G. et al. Nucleophilic addition to acetylenes in superbasic catalytic systems. 12. Vinylation of lupinine. Russian Chemical Bulletin 53, 242–244 (2004). https://doi.org/10.1023/B:RUCB.0000024856.57354.85

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  • DOI: https://doi.org/10.1023/B:RUCB.0000024856.57354.85

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