1. Lewis Acid Activation of Oxaziridines for Hydrocarbon Oxidation
Tehshik Peter Yoon, University of Wisconsin-Madison
The interaction between a drug and its target protein is typically mediated by hydrogen bonds between oxygen- and nitrogen-containing functional groups on the drug and receptors on the protein. The specificity and strength of this interaction is dictated by the arrangement of the drug’s functional groups in space. The ultimate starting materials for most synthetic organic compounds, however, are simple petrochemical hydrocarbons that do not bear functional groups, cannot hydrogen bond, and are not stereochemically well-defined. Thus, the development of methods for the selective installation of functional groups onto unfunctionalized hydrocarbon substrates is a fundamental challenge in synthetic organic chemistry.
We are exploring the use of oxygen- and nitrogen-rich compounds called oxaziridines to effect selective functionalizations of hydrocarbons. The pattern in which new functional groups are installed depends upon the identity of the catalyst, allowing for the synthesis of a variety of structures from the same starting materials.