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

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

doi:10.1351/pac200678071357

Publicly Available Published by De Gruyter January 1, 2009

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

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

From the journal Pure and Applied Chemistry

https://doi.org/10.1351/pac200678071357

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.

Keywords: alkaloid synthesis; allylic organoboranes; azaadamantanes; boraadamantanes; chiral cyclohexene derivatives; nitrogen bicyclic compounds; nitrogen cage compounds

Conference

International Meeting on Boron Chemistry (IMEBORON-XII), International Symposium on Boron Chemistry, IMEB, Boron Chemistry, 12th, Sendai, Japan, 2005-09-11–2005-09-15

Published Online: 2009-01-01

Published in Print: 2006-01-01

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

Abstract

Conference

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