Development of a One-Pot Tandem Reaction Combining Ruthenium-Catalyzed Alkene Metathesis and Enantioselective Enzymatic Oxidation To Produce Aryl Epoxides

We report the development of a tandem chemoenzymatic transformation that combines alkene metathesis with enzymatic epoxidation to provide aryl epoxides. The development of this one-pot reaction required substantial protein and reaction engineering to improve both selectivity and catalytic activity. Ultimately, this reaction converts a mixture of alkenes into a single epoxide product in high enantioselectivity and moderate yields and illustrates both the challenges and benefits of tandem catalysis combining organometallic and enzymatic systems.