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

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 diffracti...

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Bibliographic Details
Published inRussian journal of organic chemistry Vol. 42; no. 8; pp. 1225 - 1231
Main Authors Vatsadze, S. Z., Tyurin, V. S., Zatsman, A. I., Manaenkova, M. A., Semashko, V. S., Krut'ko, D. P., Zyk, N. V., Churakov, A. V., Kuz'mina, L. G.
Format Journal Article
LanguageEnglish
Published NEW YORK Springer Nature 01.08.2006
Springer Nature B.V
Subjects
Chemistry
Chemistry, Organic
NMR spectroscopy
Organic chemistry
Physical Sciences
Reaction mechanisms
Redox reactions
Ring opening
Science & Technology
Stereoselectivity
AGENT
3,7-DIAZABICYCLO<3.3.1>NONAN-9-ONES
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Summary: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.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428006080215