Jacobsen Group Research


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Introduction


Our program is dedicated to the discovery of practical catalytic reactions, and to the application of state-of-the art mechanistic and computational techniques to the analysis of those reactions. Over the past several years, we have sought and identified new classes of chiral catalysts, and several of these have found widespread application in industry and academia. These include metal-salen complexes for asymmetric epoxidation, conjugate additions, and hydrolytic kinetic resolution of epoxides; copper-diimine complexes for asymmetric aziridination; chromium-Schiff base complexes for a wide range of enantioselective pericyclic reactions; and organic hydrogen bond-donor catalysts for activation of neutral and cationic electrophiles. Our mechanistic analyses of these catalytic systems have helped uncover general principles for future catalyst design, including electronic tuning of enantioselectivity, cooperative homo- and hetero-bimetallic catalysis, hydrogen-bond donor asymmetric catalysis, and anion binding catalysis.


While the identification of useful catalysts represents an immediate goal of our work, the broader objective is to help lay the foundation for the rational design of functional molecules. Despite the organic chemists’ advanced understanding of structure, bonding, and reactivity principles, the discovery and optimization of functional molecules of any type (catalysts, medicines, materials) remains a largely empirical endeavor. With the goal of identifying general design principles, we apply the most rigorous methods of physical-organic chemistry to elucidate the mechanism of action of effective catalysts, with an emphasis on learning about the attractive and destabilizing interactions in transition structures. We think this will lead to insights into how to devise either improved catalysts for known reactions, or brand-new classes of catalysts for novel applications. And, in the long term, we hope this knowledge will allow scientists to approach the highly ambitious and important goal of rational design of both novel catalysts and other functional small molecules.


You can learn about some of the representative efforts from our lab by clicking on any of the following topics:


Catalyst Discovery


Mechanism


Synthetic Applications


Reaction Gallery