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Organic Chemistry

Optical image of the crystallized RNA precursor D-ribo-amino-oxazoline
Image: Optical image of the crystallized RNA precursor D-ribo-amino-oxazoline; courtesy of Professor Jason Hein.

The Organic Division at UC Merced has a strong background in physical organic chemistry that empowers the development and understanding of synthetic reactions. Matt Meyer investigates new mechanistic methodologies for the study of asymmetric transformations of relevance to medicinal chemistry. Ryan Baxter and Ben Stokes are developing new catalytic reactions of inexpensive feedstock chemicals. Ryan uses kinetic analysis to guide the development of metal-catalyzed single-electron transformations, while Ben investigates catalytic asymmetric transformations backed by classical physical organic techniques.

Representative Publications

  • Stokes, B. J.; Bischoff, A. J.; Sigman, M. S. "Pd(quinox)-Catalyzed Allylic Relay Suzuki Reactions of Secondary Homostyrenyl Tosylates via Alkene-Assisted Oxidative Addition" Chem. Sci. 2014, 5, 2336
  • Stokes, B. J.; Opra, S. M.; Sigman, M. S. "Palladium-Catalyzed Allylic Cross-Coupling Reactions of Primary and Secondary Homoallylic Electrophiles" J. Am. Chem. Soc. 2012, 134, 11408
  • H. Zhu, M. P. Meyer. "Cationic Intermediates in Friedel-Crafts Acylation: Structural Information from Theory and Experiment." Chem. Comm. 2011, 47, DOI: 10.1039/c0cc02286a
  • Giagou, T.; Meyer, M. P. "Mechanism of the Swern Oxidation: Significant Deviations from Transition State Theory." J. Org. Chem. 2010, 75
  • M. P. Meyer, J. P. Klinman. "Investigating Inner Sphere Reorganization via Secondary Kinetic Isotope Effects in the Hydrogen Tunneling Reaction Catalyzed by Soybean Lipoxygenase." J. Am. Chem. Soc. 2010, 132
  • iagou, T.; Meyer, M. P. "Kinetic Isotope Effects in Asymmetric Reactions." Chem. Eur. J. 2010, 16, 10616-10628.