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Pure Appl. Chem., 2006, Vol. 78, No. 7, pp. 1357-1368

Construction of nitrogen bicyclic and cage compounds with the use of allylic organoboranes

Yu. N. Bubnov1,2, N. Yu. Kuznetsov1, M. E. Gurskii2, A. L. Semenova2, G. D. Kolomnikova1 and T. V. Potapova2

1 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119991 Moscow, Russian Federation
2 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

Abstract: It is shown that reactions of triallylborane with pyrrole, pyridines, isoquinolines, lactams, 1-pyrroline, and acetylenes offer versatile methodology for the construction of various bicyclic and polycyclic nitrogen compounds, some of which are skeletally related to important classes of alkaloids. Optically active 3-borabicyclo[3.3.1]non-6-enes are useful precursors for synthesis of chiral 3-aza- and 3-thiabicyclo[3.3.1]non-6-enes, as well as derived chiral cyclohexenoid systems. The convenient methodology for the transformation of 1-boraadamantanes into 1-azaadamantanes is also discussed.