Presented herein is a methodology for the oxygenation of alpha- beta unsaturated ketones (enones) based on a mechanistic analogy from vitamin K oxidation. The primary thrust of this transformation lies in its potential ability for the concise introduction of contiguous stereocenters in which the C-O bonds of a newly generated epoxy alcohol have a cis relationship. A previously developed non-enzymatic model which mimics vitamin K oxidation is utilized for this proposal. Because many chemical compounds used as pharmaceuticals and therapeutics for the treatment of various medical ailments bear stereocenters, the development of synthetic methods that enable the concise introduction of asymmetry are highly coveted, and merit such investigation.
