Abstract
The development of new strategies for enabling regiocontrol in a variety of metal-catalyzed processes will be discussed. In one area, a variety of catalytic reductive coupling processes have been developed. The processes provide convenient alternatives to 1,2-additions to carbonyls and 1,4-additions to enones, without requiring the generation of metallated nucleophiles commonly employed. Methodological advances, detailed mechanistic analysis, and complex synthetic applications will be described. Using the knowledge gained from this effort, regiocontrol has been developed in a broader range of processes, involving simple additions such as the hydrosilylation of allenes. Finally, developments in catalytic C-H bond oxidations using both enzymatic and small molecule catalysis are under study and will be briefly described.
About the speaker
Prof John Montgomery received his PhD at Colorado State University in 1991. He was postdoctoral fellow at the University of California at Irvine from 1991 to 1993. He was faculty at Wayne State University from 1993 to 2005. He joined the University of Michigan in 2005, and is currently Margaret and Herman Sokol Professor in Medicinal or Synthetic Chemistry.
Prof Montgomery’s research interests focus on the use of transition metals in reaction discovery, synthetic methodology development, mechanistic chemistry, and complex molecule synthesis. A number of new nickel-catalyzed reactions have been discovered in his laboratory involving the reductive coupling of two π-components with a reducing agent. Among these, the reductive coupling of aldehydes and alkynes, enones and alkynes, and aldehydes and allenes have been most extensively developed. Total or formal syntheses completed by Prof Montgomery's research group using nickel-catalyzed reductive couplings as key steps include several members of the allopumiliotoxin, kainic acid, and domoic acid families of natural products as well as testudinariol A, isogeissoschizine, aigialomycin D, and pentalenene. Other new catalytic reactions developed include the reductive cycloaddition of enals and alkynes, the [4+2+1] cycloaddition of dienes, alkynes, and diazoalkanes, the crossed cycloaddition of cyclopropyl ketones and enones, the three-component coupling of enoates, aryl iodides, and aldehydes, and several coupling processes involving redox isomerization. Other current interests include the discovery of new glycosylation methods and their application in collaborative projects involving enzymatic C-H oxidation reactions.
Prof Montgomery received numerous awards including the Pfizer Michigan Green Chemistry Award, American Chemical Society Arthur C. Cope Scholar Award, and National Science Foundation CAREER Award, etc. He is a Fellow of the American Association for the Advancement of Science.
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