CAREER: Synthetic and Mechanistic Development of New Desymmetrization

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The focus of this research is the chiral, non-enzymatic desymmetrization of meso dicarboxylic esters. The methodology, based on the monohydrolysis of symmetrical diesters, results in the production of half acid esters and represents an extremely efficient entry to the preparation of valuable enantiomerically pure starting materials. Enantioselectivity is achieved by the use of quinine-based phase transfer reagents and may be of general utility within the pharmaceutical industry. Dr. Niwayama's educational efforts will focus on the development of a course that interweaves industrial research with traditional academic chemistry.With this CAREER award, the Organic and Macromolecular Chemistry Program is supporting the research and educational efforts of Dr. Satomi S. Niwayama in the Chemistry Department at Oklahoma State University. Professor Niwayama will focus her work on the development of processes that can selectively distinguish between two identical ester groups contained in the same molecule. The process will allow for the preparation of only one of the two possible mirror image products that could result. The methodology is expected to be a very inexpensive way to produce important chemical intermediates used by pharmaceutical companies The educational activities of the award will center on curriculum improvement and will include the development of a new course entitled "Industrial Chemistry."