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

在这项由化学系化学合成计划资助的项目中，东南路易斯安那大学化学与物理系的黛布拉·多利弗教授将与阿拉巴马大学塔斯卡卢萨分校的凯文·肖内西教授和蒂莫西·斯诺登教授合作，研究合成方法，以生产单一几何构型的N-杂原子亚胺，并将这些化合物应用于不对称胺的合成。主要目的有三：1)研究钯催化的N-杂原子取代的亚胺基卤化物与多种偶联对的偶联反应，2)通过合成N-杂原子的亚胺基金属化合物，将亚胺物种在钯催化的偶联反应中的作用从有机卤化物转化为金属有机试剂；3)合成氮杂原子基团中含有不对称中心的几何控制的N-杂原子亚胺衍生物，并研究这些化合物对亲核加成反应的表面选择性。本项目对基础生物科学、制药和农业工业具有重要影响，因为它将为化学合成具有强大生物活性的复杂分子提供重要的手性胺。该项目还为本科生提供了为物理学领域的职业生涯做准备的培训，考虑到在PI的机构中，第一代大学生和在物理学领域代表性不足的群体所占比例很高，这一点非常重要。

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.