CAREER: Novel Methods for Regio-, Stereo-, and Chemo-selectivity Remote to Functional Groups

化学部化学合成计划支持贾斯汀·莫尔教授的这一项目，开发有助于合成复杂分子的新催化剂分子。莫尔教授是伊利诺伊大学芝加哥分校化学系的教员。他的研究计划与开发新的教育工具相结合，这些工具可以用来向科学学习者解释复杂的概念。在研究方面，莫尔教授和他的学生试图控制含有未配对电子或负离子的高活性分子的行为。这些“中间体”被形成，然后转化为目标分子的生产，在目标分子中，所需原子的特定空间排列很难使用目前可用的方法获得。该项目在有机合成、有机金属化学和物理有机化学领域做出了贡献，并建立了在医学、农业、生物化学和材料科学中具有潜在长期应用的新分子。在教育方面，莫尔教授正在努力通过让K-12年级的儿童参与的外联活动来教育年轻学生，并增加代表不足的学生的实验室研究机会。在这一总体努力中，有一项向中学生介绍催化概念的计划。催化剂是帮助反应在不被消耗的情况下更快地朝着理想目标进行的分子。通过帮助学生了解催化剂是如何反应的，莫尔教授能够向学生传授构成现代化学方法基础的许多关键概念。莫尔教授的教育计划还包括一项努力，找出大学年龄的有机化学学生，这些学生容易在空间识别任务中遇到困难。这些困难会阻碍他们的教育，所以他的计划是及早发现问题，以便及时为学生提供额外的帮助，以确保他们的长期成功。第一排过渡金属是产生活性有机自由基中间体的有吸引力的催化剂。这些自由基物种特别适合于与共轭烯烃的新型区域和立体选择性偶联反应。这项研究旨在开发这种转化的新变种，在合成复杂分子方面具有特殊用途，适用于合成天然产品、功能材料、农用化学品和生化探针。这种方法探索了共轭二烯酸酯反应中位置选择性的控制。这项研究利用对这些阴离子中间体的电子结构的洞察来克服与两亲核试剂在成键位置上的典型选择性。利用这一概念合成有机氟化合物揭示了一种前所未有的立体控制元素，具有产生有价值的、立体化学丰富的有机氟化合物的潜力。这项研究还试图理解解释这种新的立体控制效应的基本化学概念。该教学计划利用化学反应作为平台，通过有形的演示向中学生介绍金属催化的概念。教育计划的第二部分力求找出学习立体化学概念有困难的学生，并提供改善教育结果的早期干预措施。这些组成部分涉及多个层面的科学发展。

The Chemical Synthesis Program of the Chemistry Division supports this project by Professor Justin Mohr to develop new catalyst molecules that aid in the synthesis of complex molecules. Professor Mohr is a faculty member in the Department of Chemistry at the University of Illinois at Chicago. His research program is combined with the development of new educational tools that can be used to explain complex concepts to science learners. On the research front, Professor Mohr and his students seek to control the behavior of highly reactive molecules that contain either an unpaired electron or an anion. These "intermediates" are formed and then converted into the production of target molecules where the specific spatial arrangement of the atoms required is difficult to obtain using currently available methods. This project contributes to the fields of organic synthesis, organometallic chemistry, and physical organic chemistry and builds new molecules with potential long-range applications in medicine, agriculture, biochemistry, and materials science. On the educational front, Professor Mohr is working to educate young students through outreach activities that involve children in grades K-12 students, and to increase laboratory research opportunities for underrepresented students. Within this overall effort is a plan to introduce the concept of catalysis to middle school students. Catalysts are molecules that help reactions proceed faster toward desirable targets while not being consumed. By helping students to understand how catalysts react, Professor Mohr is able to teach the students many of the key concepts that form the foundation of modern chemical methods. Professor Mohr's education plan also includes an effort to identify college age organic chemistry students that are prone to have difficulty with spatial recognition tasks. Such difficulties can impede their education, so his plan is to identify the problem early so that extra help can be provided to the students in a timely fashion so as to ensure their long-term success. First-row transition metals are attractive catalysts for generating reactive organic radical intermediates. These radical species are particularly suited to novel regio- and stereoselective coupling reactions with conjugated alkenes. This research seeks to develop new variants of such transformations that have specific uses in the synthesis of complex molecules applicable to the synthesis of natural products, functional materials, agrochemicals, and biochemical probes. This approach explores control of site-selectivity in reactions of conjugated dienolates. The research uses insights into the electronic structure of these anionic intermediates to overcome the typical selectivity in the location of bond formation with ambident nucleophiles. Use of this concept to synthesize organofluorine compounds reveals an unprecedented stereocontrol element with the potential to generate valuable, stereochemically rich organofluorine compounds. The research also seeks to understand the fundamental chemical concepts that explain this novel stereocontrol effect. The educational plan makes use of chemical reactivity as a platform to introduce the concept of metal catalysis to middle school students through a tangible demonstration. A second portion of the educational plan seeks to identify students at risk for difficulty in learning stereochemical concepts and to provide early interventions that improve educational outcomes. These components address scientific development at multiple levels.