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

Author： Vatsadze S.   Tyurin V.   Zatsman A.   Manaenkova M.   Semashko V.   Krut’ko D.   Zyk N.   Churakov A.   Kuz’mina L.  

Publisher： MAIK Nauka/Interperiodica

ISSN： 1070-4280

Source： Russian Journal of Organic Chemistry, Vol.42, Iss.8, 2006-08, pp. : 1225-1231

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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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