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New stereoselective intramolecular redox reaction in the system of 3,7-diazabicyclo[3.3.1]nonan-9-one
Authors:S. Z. Vatsadze  V. S. Tyurin  A. I. Zatsman  M. A. Manaenkova  V. S. Semashko  D. P. Krut’ko  N. V. Zyk  A. V. Churakov  L. G. Kuz’mina
Affiliation:(1) Moscow State University, Moscow, 119992, Russia;(2) Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia
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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