Lewis Acid Activation of Oxaziridines for Hydrocarbon Oxidation

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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
drugs 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 catalysts that we have found
to be optimal for these processes are
inexpensive, environmentally innocuous copper(II)
salts.