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

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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.