Project Summary Chiral, nonracemic molecules are highly important in the areas of organic synthesis, material science and chemical biology. They are also of great value to agrochemical and pharmaceutical industries because the three-dimensional structures of chiral molecules allow for the access to broader chemical space in drug discovery. Therefore, the development of catalytic methods that enable the generation of chiral molecules with high enantiopurity is important not only to academic research, but also to pharmaceutical industries, and to human health. Organoboron compounds are useful building blocks in organic synthesis. The boryl group is amenable to a variety of stereospecific chemical transformations. More importantly, the vacant p- orbital of the boron atom can stabilize an anion or a radical in the neighboring carbon atom. This unique property has facilitated the emergence of many innovative catalytic processes to generate enantioenriched organoboronates. In this regards, our group has established a research program centered on asymmetric synthesis using organoboron compounds. We particularly aim to address the challenges in enantioselective synthesis of chiral molecules that are difficult to access by conventional methods. In this proposal, we seek to develop catalytic asymmetric transformations using organoboron compounds by exploiting the novel reactivities of α-boryl metal complexes and α-boryl radicals. Through our continued collaboration with experts in computational chemistry, we will further our understanding of the reaction mechanisms, which will guide us in the direction of transformative reaction design. Meanwhile, the studies will allow for the access to enantioenriched molecules that are valuable for organic synthesis and relevant to drug discovery.