New Methods for the Stereoselective Synthesis of Organic Compounds

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Most important molecules found in nature (enzymes, proteins, RNA, DNA, etc.) are chiral and cannot be superimposed upon their mirror image. Yet, these compounds are the most challenging to selectively synthesize due to their inherent similarity between various chemical structures. Normally, when a chiral molecule is produced in the laboratory, its synthesis produces a mixture containing equal amounts of two enantiomer forms, but while one form may be beneficial to health, the other may be harmful. On the other hand, small heteroaromatic rings are of central importance in the development of novel synthetic protein ligands that will eventually evolve into novel drugs. It is estimated that over 3,000 of these molecules are still unknown! The plethora of successful methodologies available in organic synthesis has reached an impressive number, but there is still a long way to go to synthesize any molecule using highly efficient methods having minimal environmental impact. The specific aim of our research will be directed towards the development of new and efficient methods for the selective (regio-, chemo-, enantio- and/or diasteroselective) synthesis of organic compounds containing mostly carbon, hydrogen, oxygen and nitrogen. As organic chemists, we always strive not only to improve existing synthetic methods, but also to develop new and more effective ones. To that effect, more powerful, greener, and protecting-group-free are still needed. This area of organic chemistry is of primary importance due to today’s necessity for enantiomerically pure compounds in a variety of related disciplines (pharmaceuticals, agrochemicals, biology, material sciences, biochemistry, food sciences, etc.). In order to achieve this, we will develop novel tools (reagents and catalysts) to help control the specificity of a given chemical transformation. Among the priorities, cyclopropane synthesis and functionalization, novel heterocycle synthesis and functionalization, highly chemoselective transformations using amides, as well as catalytic amide synthesis are the most important themes. We will also concentrate our efforts on understanding the fundamental mechanistic implications of the newly developed transformations. This will allow us to build upon observations and push the chemistry to higher limits. Finally, the synthesis of complex natural products will be pursued, since this is the ultimate ground to test the efficiency of new synthetic methodologies. Catalysis, which is featured as one of the 12 principles of Green chemistry and as one of the key strategies to use in Green chemical processes, will play a central role in the development of new methods. Overall, the fruits of our research will be extremely important for both the academic and industrial sectors, because chiral, non-racemic compounds are critical intermediates that will lead to the development of new products in fields as diverse as pharmaceutical science, agrochemical science, biology, biochemistry, food science, materials sciences, pharmacology and medicine. Considering that several chemistry-related companies are based in the greater Montreal area, we anticipate that our research will naturally strengthen and complement their existing R&D programs, thus help them hone their competitive edge in the global economy. As well, a new generation of highly qualified scientists possessing unique skills and a modern mindset on organic chemistry and green practices will be perfectly trained to join the workforce and to ensure a flow of unique expertise into the marketplace. In addition, the potential for discoveries that will emerge from our research will open the door to innovation, which, ultimately, will create a healthier and cleaner environment for the Canadian population at large.