Joseph M. Fox
University of Delaware
272 Brown Lab
Newark, DE 19716
(b. 1971) A.B., 1993, Princeton University; M. S., 1994, Columbia University; Ph.D., 1998 Columbia University; National Institutes of Health Postdoctoral Fellow, 1999 – 2001, Massachusetts Institute of Technology
Research in the Fox group centers on the development of new types of chemical reactions, the application of these new reactions to the synthesis of natural occurring and designed molecules with biological function, and in the use of design concepts in organic synthesis for applications in materials science. The nature of the research program is highly multidisciplinary, and involves active collaborations with groups in peptide chemistry, bioorganic chemistry, surface science, computational chemistry, materials science, and radioimaging.
Our work focuses on the idea of using strain as a design principle in synthesis. The basic concept is that high energy molecules have unusual— and therefore interesting— reactivity. To this end, the Fox group has developed a number of new reactions and transformations of chiral cyclopropenes, methylenecyclopropenes and trans-cycloalkenes. The applications extend into natural products synthesis and pharmaceutical research. A new type of strain driven bioorthogonal ligation further extends the applications to bioorganic chemistry, and molecular imaging.
Our group is interested in the design and utilization of new catalyst types. In one area, we have developed the first general conditions for Rh-catalyzed intermolecular reactions of alkyldiazo compounds. Ordinarily, intermolecular chemistry of carbenoids from alkyldiazo compounds is precluded by beta-hydride elimination. Current interests include the development of new classes of Rh-catalysts for enantioselective transformations of alkyldiazo compounds.
Our group is also actively investigating the origin of asymmetric induction in salen-based catalysis. To this end, we have designed a novel class of metallofoldamers. We have shown how these macromolecules can provide unusual insight into the conformation of salenmetal complexes and the mechanisms by which they induce asymmetry.
- A. DeAngelis, O. Dmitrenko, G. P. A. Yap and J. M. Fox “Chiral Crown Conformation of Rh2(S-PTTL)4: Enantioselective Cyclopropanation with α-Alkyl-α- diazoesters,” J. Am. Chem. Soc., (2009) 131, 7230 – 7231.
- V. Tarwade, X. Liu, N. Yan and J. M. Fox “Directed Carbozincation Reactions of Cyclopropene Derivatives,” J. Am. Chem. Soc., (2009) 131, 5382 – 5383.
- A. DeAngelis, M. T. Taylor and J. M. Fox “Unusually reactive and selective carbonyl ylides for three-component cycloaddition reactions,” J. Am. Chem. Soc., (2009)131, 1101 – 1105.
- M. L. Blackman, M. Royzen and J. M. Fox “The Tetrazine Ligation: Fast Bioconjugation based on Inverse-electron-demand Diels-Alder Reactivity,” J. Am. Chem. Soc., (2008) 130, 13518 – 13519.
- M. Royzen, G. P. A. Yap and J. M. Fox “A Photochemical Synthesis of Functionalized trans-Cyclooctenes Driven by Metal Complexation,” J. Am. Chem. Soc., (2008)130, 3760 – 3761.
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