Regio- and stereoselective hydrogenolysis of optically active diols via transfer hydrogenation: Synthesis of alpha-arylpropionic acids

Asymmetric synthesis of alpha-arylpropionic acids, Ibuprofen 1b, Naproxen 1 c, and Flurbiprofen 1d have been achieved by employing Sharpless asymmetric dihydroxylation followed by the stereoselective hydrogenolysis of the chir al diols coupled with Jones' oxidation as the key steps. The regio- and ste reoselective hydrogenolysis of the chiral diols at the benzylic position pr oceeds with retention of configuration for all the substrates studied.