PO Box 644630
Pullman, WA 99164-4630
Harvard University, Cambridge, MA
Ph.D. Chemistry, 1968
University of North Carolina, Chapel Hill, NC
Professor Cooke earned his Ph.D. degree in chemistry at the University of North Carolina, Chapel Hill (1968) and did postdoctoral research with Nobel laureate E.J. Corey at Harvard University and with J.P. Collman at Stanford University, before joining the faculty at WSU in 1971.Our research efforts are directed primarily toward the development of new synthetic methods in both organic and organo-transtition metal chemistry. We are presently exploring a new approach to conjugate addition reactions in which normally competing 1,2-addition reactions are suppressed by the presence of an adjacent unit of negative charge. An example of such charge-directed addition reactions using an unsaturated ylide is shown below.
We are also investigating a variety of metal-halogen exchange-initiated cyclization reactions. Rapid lithium-iodine exchange reactions are used to generate reactive nucleophilic centers which then undergo intramolecular conjugate addition reactions. An example showing the utility of this approach in multiple-ring synthesis is shown below.
I have recently begun a study of a new class of Michael acceptors which represent the first examples of boron-activated nucleophilic additions to olefins. Such reactions are made possible by the steric suppression of reactions of nucleophiles with the acidic boron atom.
- Cooke, Jr., M. P., “Boron-Activation of Acetylenes to Nucleophilic Addition Reactions”, J. Org. Chem. (1994) 59 2930
- Cooke, Jr., M. P. and Gopal, D., “Tandem Metal-Halogen Exchange-Initiated Conjugate Addition Reactions of Acetylenic Esters”, J. Org.Chem. (1994) 59 260
- Cooke, Jr., M. P. and Gopal, D., “Stereoselective Construction of Functionalized Bicyclic Carbocycles Through Metal-Halogen Exchange-Initiated Sequential Conjugate Addition Reactions”, Tetrahedron Lett. (1994) 35 2837
- Cooke, Jr., M. P. and Pollock, C. L., “Charge-Directed Conjugate Addition Reactions of Silylated alpha-beta-Unsaturated Amidate Anions”, J. Org. Chem. (1993) 58 7474
- Cooke, Jr., M. P., “Metal-Halogen Exchange-Initiated Intramolecular Conjugate Addition Reactions of Conjugated Acetylenic Esters”, J. Org.Chem. (1993) 58 6833