Abstract
Reductive tetraallylation of pyridine-3-and pyridine-4-carboxylic acids with triallylborane in the presence of propan-2-ol proceeded stereoselectively to yieldtrans-2,6-diallyl-3- andtrans-2,6-diallyl-4-(1-allyl-1-hydroxybut-3-en-1-yl)-1,2,5,6-tetrahydropyridines, respectively. Under the same conditions, the reaction with pyridine-2-carboxylic acid gave a mixture oftrans- andcis-2,6-diallyl-2-(1-allyl-1-hydroxybut-3-en-1-yl)-1,2,5,6-tetrahydropyridines in a ratio of 57:43. When 2,6-diphenylpyridine-4-carboxylic acid reacted with triallylborane, only the carboxylic group underwent reductive diallylation. When heated with triallylborane ino-xylene (130–133°C, 7 h),trans-2,6-diallyl-4-(1-allyl-1-hydroxybut-3-en-1-yl)-1,2,3,6-tetrahydropyridine was converted to the correspondingcis-isomer. The stereochemistry oftrans-2,6-diallyl-3-(1-allyl-1-hydroxybut-3-en-1-yl)-1,2,5,6,-tetrahydropyridine was confirmed by X-ray diffraction analysis.
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Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 2320–2326, November, 1998.
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Bubnov, Y.N., Demina, E.E., Bel'sky, V.K. et al. Stereoselective reductive tetraallylation of pyridinecarboxylic acids with triallylborane. Russ Chem Bull 47, 2249–2255 (1998). https://doi.org/10.1007/BF02494291
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DOI: https://doi.org/10.1007/BF02494291