New stereoselective intramolecular redox reaction in the system of 3,7-diazabicyclo[3.3.1]nonan-9-one |
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| 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 |
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| Institution: | (1) Moscow State University, Moscow, 119992, Russia;(2) Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia |
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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-diazabicyclo3.3.1]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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