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Allylboranes: reductive mono andtrans-diallylation of aromatic nitrogen-containing heterocyclic compounds

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Abstract

Reductiveα-mono- and stereoselective trans-α,α′-diallylation of aromatic nitrogencontaining heterocycles by allylic boron derivatives have been discovered. A method for thetrans-to-cis isomerization oftrans-2,5-diallylpyrrolidines andtrans-2,6-diallyl-1,2,5,6-tetrahy-dropyridines by heating with allylboranes has been developed. The above reactions unite the chemistry of nitrogen-containing heterocycles and the chemistry of organoboron compounds on a new level.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    Yu. N. Bubnov

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1203–1216, July, 1995.

The author is sincerely grateful to his colleagues E. A. Shagova, S. V. Evchenko, L. I. Lavrinovich, A. Yu. Zykov, E. V. Klimkina, and A. V. Ignatenko for their active participation in this work, as well as to M. E. Gurskii, I. D. Gridnev, and A. V. Geiderikh for useful advice and critical notes.

This study was financially supported in part by the Russian Foundation for Basic Research (Grant No. 93-03-18193) and the International Science Foundation (Grant M3Y 000).

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Bubnov, Y.N. Allylboranes: reductive mono andtrans-diallylation of aromatic nitrogen-containing heterocyclic compounds. Russ Chem Bull 44, 1156–1170 (1995). https://doi.org/10.1007/BF00700882

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