The Chemical Catalysis Program of the Chemistry Division supports the project by Professor Viresh H. Rawal. Professor Rawal is a faculty member in the Department of Chemistry at the University of Chicago. He is investigating the design and use of novel small molecule catalysts that, like enzymes, can activate reactants through hydrogen bond interactions and thereby catalyze highly selective reactions. This metal-free acceleration of reactions is not only of fundamental interest, but also has benefits to society, since metal impurities are undesirable in consumer products, such as specialty materials and medicines. The research focuses on the development of new hydrogen bonding catalysts, including bifunctional catalysts, for the synthesis of chiral substances. Such compounds possess mirror asymmetry and have considerable economic and biomedical importance. These projects provide training in chemical synthesis, problem solving, and oral and written communication to researchers at all levels. Through this work, Professor Rawal provides scientific research opportunities for students from underrepresented groups.
New classes of chiral hydrogen bond donor compounds are being developed and examined as catalysts for asymmetric reactions. These novel hydrogen (H)-bond donor scaffolds are expected to expand the classes of reactions that can be rendered enantioselective and lead to improvements in the effectiveness and substrate scope of other reactions. A particular focus is on the study of catalysts possessing two or more H-bond donor groups, enabling the activation of substrates containing a carbonyl group, an important functional group for organic synthesis. The catalysts under study probe the importance of the distance between the two donor hydrogens, as well as their acidity, for effective activation of the carbonyl group. The investigations, which are carried out in conjunction with mechanistic, computational, and crystallographic studies, provide information on the activation capabilities of the new hydrogen bond donor scaffolds. Three distinct catalyst scaffolds are under development. The structural and reactivity properties of each are examined in a wide range of reactions. Studies show that the catalysts are highly active, requiring only 0.1-1 mol% loading, so they provide environmentally friendly solutions for chemical synthesis. The work opens access to a wide range of chiral compounds, of importance for natural product synthesis, drug development, and materials chemistry. Outreach activities involve participation by high-school students, particularly those from underrepresented groups.
