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

Bubnov, Yu. N.; Kuznetsov, N. Yu.; Gurskii, M. E.; Semenova, A. L.; Kolomnikova, G. D.; Potapova, T. V.

doi:10.1351/pac200678071357

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

http://dx.doi.org/10.1351/pac200678071357

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

Yu. N. Bubnov^1,2, 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.