CAREER: Enantioselective Syntheses of Organoboron Compounds via Transition-Metal Catalysis

在化学系化学合成项目的支持下，奥本大学的陈明博士正在研究制造有机硼化合物的新方法，有机硼化合物是重要的化学构件。陈教授和他的研究小组正在开发反应，使分子在同一个碳原子上具有两个不同的硼基基团（二硼基试剂），并控制手性或立体化学，然后依次选择性地利用每个硼基基团将新的分子片段连接到中心碳上。这种策略有可能促进对有机合成、材料科学以及农业化学和制药工业有价值的新型分子构建块的模块化访问。陈教授和他的团队还通过奥本大学暑期科学研究所开展外展活动，为K-12学生提供动手研究机会和手性分子介绍（不可重叠的镜像，如右手和左手），以帮助提高追求STEM职业生涯的动力手性非外消旋有机硼化合物是有机合成、材料科学和药物化学中的重要组成部分。手性有机硼化合物的多功能合成用途为进一步衍生化提供了一个极好的平台，以产生有价值的化学合成下游产品。Chen博士和他的研究小组正在开发新的不对称转化，以从具有两个化学上不同的硼基的1，1-双硼基烷烃制备手性、非外消旋有机硼化合物。钴催化的硼氢化反应也正在研究中，以获得对映体富集的1，1-bisborylalkanes，以支持这些化合物作为更复杂的有机硼结构的构建块的研究。1，1-bisborylalkanes与两个化学上不同的硼基基团的反应性的基础研究，预计将提供洞察如何最好地利用这些试剂的性质，以访问类的对映体富集的有机硼化合物，是无法通过目前的方法。这些活动为不同的研究生和本科生群体提供了现代立体控制合成化学的良好培训基础。该奖项反映了NSF的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。

With the support of the Chemical Synthesis Program in the Division of Chemistry, Dr. Ming Chen of Auburn University is studying new ways to make organoboron compounds, which are important chemical building blocks. Professor Chen and his research group are developing reactions to make molecules with two distinct boryl groups on the same carbon atom (diboryl reagents) with control of handedness or stereochemistry and then to sequentially and selectively utilize each boryl group to attach new molecular fragments to the central carbon. This strategy has the potential to facilitate modular access to novel molecular building blocks that are valuable to organic synthesis, material science, as well as the agrochemical and pharmaceutical industries. Professor Chen and his team are also engaged in outreach activities through the Auburn University Summer Science Institute to provide K-12 students with hands-on research opportunities and an introduction to chiral molecules (non-superimposable mirror images like right- and left-hands) to help boost motivation in pursuing careers in STEM (science, technology, engineering, and mathematics)-related disciplines.Chiral, non-racemic organoboron compounds are important building blocks in organic synthesis, material science, and medicinal chemistry. The versatile synthetic utility of chiral organoboron compounds provides an excellent platform for further derivatization to generate valuable downstream products for chemical synthesis. Dr. Chen and his research group are developing new asymmetric transformations to prepare chiral, non-racemic organoboron compounds from 1,1-bisborylalkanes with two chemically distinct boryl groups. A cobalt-catalyzed hydroboration is also being studied to access enantioenriched 1,1-bisborylalkanes to support the investigation of these compounds as building blocks for more complex organoboron structures. Fundamental studies on the reactivity of 1,1-bisborylalkanes with two chemically distinct boryl groups are expected to provide insight into how to best leverage the properties of these reagents to access classes of enantioenriched organoboron compounds that are not accessible through current methodologies. These activities are providing an excellent training ground in modern, stereocontrolled synthetic chemistry for a diverse group of graduate and undergraduate students.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.