Stereoselective reductive tetraallylation of pyridinecarboxylic acids with triallylborane |
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| Authors: | Yu N Bubnov E E Demina V K Bel'sky G V Zatonsky A V Ignatenko |
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| Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation;(2) A. N. Nesmeyahov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation;(3) L. Ya. Karpov Scientific Research Institute of Physical Chemistry, 10 ul. Vorontsovo pole, 103064 Moscow, Russian Federation |
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| 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.
Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 2320–2326, November, 1998. |
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| Keywords: | pyridinecarboxylic acids reductive allylboration triallylborane trans-cis isomerization |
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