RUI: Synthesis of Single Geometric Isomers of N-Substituted Ketimines: Starting Materials for the Synthesis of Asymmetric Amines

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In this project funded by the Chemical Synthesis program of the Chemistry Division, Professor Debra Dolliver of the Department of Chemistry & Physics at Southeastern Louisiana University, in collaboration with Professors Kevin Shaughnessy and Professor Timothy Snowden from the University of Alabama, Tuscaloosa, will study synthetic methodology to produce N-heteroatomic imines in single geometries and applying these compounds for the synthesis of asymmetric amines. There are three specific aims: 1) to investigate the palladium-catalyzed coupling of N-heteroatomic-substituted imidoyl halides with a variety of coupling partners; 2) to initiate studies to reverse the role of the imine species in Pd-catalyzed coupling reactions from that of the organohalide to that of the organometallic reagent by synthesizing an N-heteroatomic imidoyl metal compound; and 3) to synthesize geometrically-controlled N-heteroatomic imine derivatives containing an asymmetric center in the heteroatomic group attached to nitrogen and investigate facial selectivity of these compounds to nucleophilic addition.This project has significant impacts on fundamental biological sciences, pharmaceutical and agricultural industries, as it would provide ready access to chiral amines important in the chemical synthesis of complex molecules of potent biological activities. The project also provides trainings for undergraduate students in preparation for careers in the physical science fields, which is very significant considering the high percentage of first generation college students and groups underrepresented in the physical sciences at the PI's institution.