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

摘要

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