Technique for the Synthesis of Difluorinated Organic Molecules Using Magnesium Bases

Baldwin, Cassidy S. (2018) Technique for the Synthesis of Difluorinated Organic Molecules Using Magnesium Bases. Undergraduate thesis, under the direction of David Colby from Department of BioMolecular Sciences, The University of Mississippi.

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Abstract

The presence of fluorine in organic molecules can confer biological advantages which are often exploited in drug development. For example, fluorine has been shown to limit drug metabolism and enhance drug distribution. However, the development of fluorinated pharmaceutics poses synthetic challenges. These challenges are especially pronounced when developing molecules with a difluoromethyl group. One difluoromethyl functional group of particular interest is the α,α-difluoro-β-amino carbonyl group, which has been seen in potential drug leads. The previous methods of accessing this group are inefficient and complex. The goal of this project was to develop a new technique to access this group by reacting α,α-difluoroenolate intermediates with unactivated imines in the presence of magnesium bases. The results showed evidence that a simpler method of the synthesizing α,α-difluoro-β-amino ketones is possible and should be further explored.

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