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New stereoselective intramolecular redox reaction in the system of 3,7-diazabicyclo[3.3.1]nonan-9-one

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Abstract

The ring opening in the 1-benzyl-5,7-dimethyl-6-oxo-1-azonia-3-azaadamantane chloride under the treatment with excess aqueous alkali led to a stereoselective formation of anti-1,5-dimethyl-7-benzyl-3-formyl-3,7-diazabicyclo[3.3.1]nonan-9-ol whose structure was established by means of X-ray diffraction analysis and NMR spectroscopy. A reaction mechanism was suggested involving an intramolecular redox hydride transfer.

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Authors and Affiliations

  1. Moscow State University, Moscow, 119992, Russia

    S. Z. Vatsadze, V. S. Tyurin, A. I. Zatsman, M. A. Manaenkova, V. S. Semashko, D. P. Krut’ko & N. V. Zyk

  2. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia

    A. V. Churakov & L. G. Kuz’mina

Authors
  1. S. Z. Vatsadze
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  2. V. S. Tyurin
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  3. A. I. Zatsman
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  4. M. A. Manaenkova
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  5. V. S. Semashko
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  6. D. P. Krut’ko
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  7. N. V. Zyk
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  8. A. V. Churakov
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  9. L. G. Kuz’mina
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Additional information

Original Russian Text © S.Z. Vatsadze, V.S. Tyurin, A.I. Zatsman, M.A. Manaenkova, V.S. Semaskho, D.P. Krut’ko, N.V. Zyk, A.V. Churakov, L.G. Kuz’mina, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 8, pp. 1244–1249.

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Vatsadze, S.Z., Tyurin, V.S., Zatsman, A.I. et al. New stereoselective intramolecular redox reaction in the system of 3,7-diazabicyclo[3.3.1]nonan-9-one. Russ J Org Chem 42, 1225–1231 (2006). https://doi.org/10.1134/S1070428006080215

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  • DOI: https://doi.org/10.1134/S1070428006080215

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