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

职业：通过过渡金属催化对映选择性合成有机硼化合物

• 批准号: 2042353
• 负责人: Ming Chen
• 金额: $ 68.5万
• 依托单位: Auburn University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2021
• 资助国家: 美国
• 起止时间: 2021-09-01 至 2026-08-31
• 项目状态: 未结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=2042353&HistoricalAwards=false
• 关键词: CAREER; Enantioselective; Syntheses; Organoboron; Compounds

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.

在化学系化学合成计划的支持下，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，通过左手或立体化学的控制，使同一碳原子上具有两个不同硼基的分子(二硼基试剂)，然后顺序地和选择性地利用每个硼基将新的分子片段连接到中心碳上。这一战略有可能促进对有机合成、材料科学以及农化和制药行业有价值的新型分子构件的模块化访问。陈教授和他的团队还通过奥本大学暑期科学研究所开展推广活动，为K-12年级的学生提供实践研究机会和手性分子(右手和左手等不可重叠的镜像)的介绍，以帮助增强人们在STEM(科学、技术、工程和数学)相关学科中追求职业生涯的动机。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的重要组成部分。手性有机硼化合物具有广泛的合成用途，为进一步的衍生化反应提供了一个很好的平台，为化学合成提供了有价值的下游产品。陈博士和他的研究小组正在开发新的不对称转化，从具有两个化学上不同的硼基的1，1-双硼烷制备手性、非外消旋的有机硼化合物。还在研究钴催化的氢硼化反应，以获得对映体富集型1，1-二硼基烷，以支持将这些化合物作为更复杂的有机硼结构的构建块进行研究。关于1，1-二硼基烷与两个不同化学基团的反应性的基础研究有望提供关于如何最好地利用这些试剂的性质来获取通过当前方法无法获得的一类富对映体有机硼化合物的见解。这些活动为不同的研究生和本科生提供了一个在现代、立体控制的合成化学方面的极好的培训基础。该奖项反映了NSF的法定使命，并通过使用基金会的智力优势和更广泛的影响审查标准进行评估，被认为值得支持。

项目成果

Stereochemical Control via Chirality Pairing: Stereodivergent Syntheses of Enantioenriched Homoallylic Alcohols

• DOI: 10.1002/anie.202107004
• 发表时间: 2021-10-04
• 期刊: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
• 影响因子: 16.6
• 作者: Gao, Shang;Duan, Meng;Chen, Ming
• 通讯作者: Chen, Ming