Sustainable Technologies for Building Molecules: Ethers, Phosphines, and Amino Acids

With the support of the Chemical Catalysis Program in the Division of Chemistry, Professor Vy Dong of the University of California, Irvine is studying the development of new catalytic reactions to expedite the synthesis of organic molecules with improved efficiency and reduced waste. Earth-abundant nickel catalysts will be investigated for the construction of C-O bonds and unnatural amino acids with precise control of three-dimensional molecular shape. The introduction of selenium into small molecules and the construction of new asymmetric phosphine ligands will also be explored using photocatalysis and copper catalysis. This project sets out to advance understanding of how to build challenging chemical bonds, while also reducing reliance on precious metals. Precisely controlling the shape of molecules is critical for optimization and fine-tuning the performance of medicines and materials; therefore, this proposal is creating tools for molecular construction to empower scientists in other fields to design future therapies and materials technologies. These activities are further expected to provide training for a diverse group of graduate, undergraduate, and high school student researchers. Professor Dong is also leading initiatives to engage students and the public in chemistry discussions via social media and increasing the visibility of role models and networking opportunities for women in chemistry. The development of new catalysts that enable sustainable methods for the enantioselective synthesis of organic molecules is essential to achieve continued advances in the preparation of medicines, materials, and biological probes. This program features catalytic strategies to address modern challenges in synthesis. Under this award, Professor Dong and her research team will pursue the following goals: (1) activating chalcogens for hydrofunctionalization, (2) designing and constructing phosphines and (3) forging novel routes to amino acids and cyclic peptides. These three primary objectives feature transition metal catalysts, including those derived from earth abundant first row metals (e.g., Ni-catalyzed asymmetric alcohol additions, Cu-phosphido transformations, and Ni-catalyzed cyano-ester and allene couplings). Efforts in these directions are focused on accessing organic structures that have been difficult to prepare by current asymmetric catalysis technologies, including chiral ethers, phosphines, and peptides. The mechanistic approach to these activities will help enable the participating graduate students to gain critical analysis and troubleshooting skills and will also engage undergraduate and high school students in chemical research at a fundamental level. 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.