These scientific project deals with synthesis and functionalization of nitrogen heterocycles catalyzed by transition metals. The first part of this project was devoted to the development of a simple and efficient reaction for the N-cyclopropylation of various nitrogen compounds. From cyclopropylboronic acid under copper oxidative coupling conditions, a wide variety of nitrogen compounds have been N-cyclopropylated. This method allows a new access to N-cyclopropylated substrates.The second part of this work deals with benzimidazoles synthesis. These nitrogen heterocycles have been obtained from amidines through a sequence involving a N-arylation reaction followed by cyclization via a C-H bond functionalization.The third part of this manuscript focuses on pyrroles synthesis. Pyrroles are known for their abundance in biologically active molecules. We have developed a new sequential one-pot procedure for poly-functionalized N-H pyrroles synthesis. Through a enaminone formation catalyzed by indium (III), followed by a palladium catalyzed heteroannulation, various N-H pyrroles have been synthesizedThe final part of this scientific project describes our approach to total synthesis of an alkaloid: the (-)-norsuavéoline. The specificity of our approach was based on the formation of pyridine ring in the beginning of the synthesis and a late formation of indole ring. To date, we have developed and optimized the pyridine synthesis from L-(-)-glutamic acid. Studies are ongoing in the laboratory to obtain the indole part and complete the synthesis of this natural product.
Synthesis and functionalization of nitrogen heterocycle catalyzed by metal transition. Toward the total synthesis of (-)-norsuaveoline.