Design, Development and Exploration of New Chiral Spirocyclic Ligands and Catalysts for Asymmetric Catalysis

点击翻译按钮获取中文摘要

With this award, the Chemical Catalysis Program of the NSF Division of Chemistry is supporting the research of Dr. Pavel Nagorny of the Department of Chemistry at the University of Michigan. Dr. Nagorny and his research team are developing catalyst scaffolds that can control how molecules interact to produce favored enantiomeric products. Enantiomers are molecules that have similar structures but are mirror images of each other (i.e. a right hand and a left hand). Different enantiomers can have distinct characteristics including therapeutic potency and properties, which is why there is a critical need for catalysts that can selectively form these molecules. The Nagorny research group has previously identified a new type of catalyst that is highly active towards controlling enantioselectivity and is easily tunable towards new types of reactions. Professor Nagorny and his students are currently investigating how these catalysts work and optimizing them for the synthesis of compound fragments that are currently found in bioactive molecules. In addition, the Nagorny group is developing heterogeneous analogues of these catalysts to improve recyclability and sustainability. These studies are being used to train a diverse group of graduate and undergraduate students. Professor Nagorny and his students are also developing instructional safety videos to improve the learning experience of students at the University of Michigan and beyond.Improvements in asymmetric catalysis are critically important for the synthesis of bioactive molecules. To address this need, Dr. Pavel Nagorny and his research group are expanding the repertoire of existing spirocyclic ligands for iridium-catalyzed hydrogenations by exploring a new C2-symmetric chiral scaffold (SPIROL). These ancillary groups possess the key structural features found in the most popular and best-performing chiral spirocyclic ligands and catalysts, but are also easy to synthesize and tune. Simultaneously, the Nagorny group is also working to improve the process efficiency and sustainability associated with the use of spirocyclic catalysts by developing immobilized variants. Immobilized chiral spirocyclic phosphoric acids are being optimized for asymmetric transformations in continuous flow. These studies are advancing tools and processes needed to accelerate asymmetric synthesis.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.