Y. Bubnov, E. Klimkina, Z. Starikova
Jun 1, 2001
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Journal
Russian Chemical Bulletin
Abstract
Reductive allylation of the bis(pyridine)dihydropyridyllithium dimer containing the 1,2- and 1,4-dihydropyridine fragments by triallylborane results mainly in trans- and cis-2,6-diallylpiperidines (60—85%), their ratio depending on the nature of the solvent. The minor reactions products are 2-allyl-1,2,3,6-tetrahydropyridine and 4,10-diallyl-3,9-diazatricyclo[6.2.2.02,7]dodecane. The unexpected formation of the latter is due to hetero-Diels—Alder condensation of intermediate products formed in the allylboration of dihydropyridines. The stereochemistry of trans- and cis-2,6-diallylpiperidines was determined from the 1H and 13C NMR spectra of the respective N,N-dimethylpiperidinium iodides. The structure of 4,10-diallyl-3,9-diazatricyclo[6.2.2.02,7]dodecane dipicrate was established by X-ray diffraction analysis.