Mechanistic and synthetic chemistry.
Department of Chemistry & Chemical Biology
12 Oxford Street
Cambridge, MA 02138
Lab Size: Greater than 10
Catalysts not only accelerate chemical reactions, but can also exert remarkable kinetic control over product distribution. My research group is interested in all aspects of selective catalysis, and especially in the design, discovery, and study of systems that mediate fundamentally interesting and useful organic reactions. The search for practical and widely applicable catalysts for organic synthesis provides a strong driving force for our research. In addition, we apply the tools of physical-organic chemistry to gain insight into the transition structure geometries and molecular recognition events that control selectivity.
The following topics in selective catalysis are currently under investigation in our laboratories:
- Asymmetric Catalysis
- Selective C- C Bond Formation and Cleavage
- Natural-Product and Diversity-Oriented Synthesis
- Mimics of Physiologically Important Enzymes
- New Approaches to Catalyst Design
The control of absolute and relative stereochemistry is an underlying goal in much of this work because of the crucial role played by the three-dimensional structure of molecules in their biological function. The development of enantioselective oxidation catalysts has been of particular interest to us, and we have succeeded in devising highly enantioselective small-molecule catalysts in which selectivity is predicated solely through non-bonded interactions. The utility of these catalysts has been illustrated in our group through their application to the synthesis of various classes of important biologically active compounds.
Zuend, S. J.; Coughlin, M. P.; Lalonde, M. P.; Jacobsen, E. N. “Scaleable catalytic asymmetric Strecker syntheses of unnatural -amino acids,” Nature 2009, 461, 968–970.
Zuend, S. J., Jacobsen, E. N. “Mechanism of Amido-Thiourea Catalyzed Enantioselective Imine Hydrocyanation: Transition State Stabilization via Multiple Non-Covalent Interactions,” J. Am. Chem. Soc. 2009, 131, 15358–15374.
Xu, H.; Zuend, S. J.; Woll, M. P.; Tao, Y.; Jacobsen, E. N. “Asymmetric Cooperative Catalysis of Strong Brønsted Acid-Promoted Reactions Using Chiral Ureas,” Science 2010, 327, 986–990.
Knowles, R. R.; Lin, S.: Jacobsen, E. N. “Enantioselective Thiourea-Catalyzed Cationic Polycyclizations,” J. Am. Chem. Soc. 2010, 132, 5030–5032.