The majority of the work in this thesis presents a new method to syntheisize imidazolines from both chiral and racemic aziridines. The purpose of synthesizing such heterocycles was for there known biological activity. Previous research in the Tepe group has developed a method to diastereoselectively synthesize racemic imidazolines from the trimethyl silyl chloride mediated (3 +2) cycloaddition of imines with azlactones. This methodology allowed access to variety of imidazolines that have been shown to inhibit NF-κB mediated gene transcription. An SAR study has been conducted in our research group on this class of compounds. The ability of the imidazolines to inhibit NF-κB mediated gene transcription was measured by human cervical epithelial (HeLa) cells and human whole blood. The result of these studies has determined which functional groups were essential for efficient inhibition of NF-κB. These studies have also determined that one imidazoline enantiomer was much more potent inhibitor than the other. Although our research group has created a diastereoselective method to synthesize imidazolines there was still not a method to synthesize chiral imidazolines. Due to the cost, time, and inefficiencies of separation of racemic imidazolines by chiral HPLC and resolution an enatioselective method was needed. This thesis represents the progress towards an enantioselective synthesis of imidazolines.
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