Monophenylation of morphinan-6-ones with diphenyliodonium iodide

By reacting lithium enolate of hydrocodone with commercially available diphenyliodonium iodide (DII), the conversion of hydrocodone into 7-phenylhydrocodone can be obtained in good amount. The DII approaches the beta-face of the enolate, resulting in enolization and epimerization of the 6-beta isomer, which is then ketonized to the stable 6-alpha epimer.