Noyori Asymmetric Hydrogenation – an electrophilic addition reaction

In 1980, the Japanese Nobel prize-winning chemist Ryoji Noyori reported that BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) complexed with ruthenium [BINAP-Ru(II)] catalyzed the asymmetric hydrogenation of alpha-(acylamino)acrylic acids or esters to give the corresponding amino acid derivatives in excellent enantiomeric yields. Several years later, it was discovered that asymmetric hydrogenation of a wide variety of functionalized olefins could be achieved utilizing BINAP-Ru(II) dicarboxylate complexes. Subsequently, it was found that oligomeric halogen-containing BINAP-Ru(II) complexes were efficient catalysts for the asymmetric hydrogenation of functionalized ketones. Following these discoveries, the reduction of both functionalized olefins and ketones using BINAP-Ru(II) in the presence of hydrogen gas became known as the Noyori asymmetric hydrogenation.

Industrial uses of this technique include the synthesis of the anti-inflammatory drug naproxen and the antibacterial agent levofloxacin.

Mechanism of the Noyori asymmetric hydrogenation reaction

Review available Thermo Scientific products for the Noyori asymmetric hydrogenation reaction: