To produce the subject alcohols useful as a synthetic intermediate, etc., for medicines by asymmetrically hydrogenating a specific carbonyl compound with hydrogen in the presence of an asymmetric hydrogenating catalyst of a transition metal, a base and an optically active nitrogen-containing organic compound.
A carbonyl compound represented by formula I (R1 and R2 are each an aromatic monocyclic ring, an aromatic polycyclic ring, etc.) is reacted with hydrogen in the presence of a transition metallic complex of a group VIII metal having an optically active ligand (preferably a phosphine ligand) at preferably (1/100) to (1/100,000) molar ratio thereof to the carbonyl compound, a base (preferably an alkali metal, a quaternary ammonium salt, etc.) in an amount of 0.5-100 equiv. for the metallic complex and an optically active nitrogen-containing organic compound (preferably an optically active amine compound) in an amount of 1-4 equiv. for the metallic complex in the case of a monoamine compound or in an amount of 0.5-2.5 equiv. for the metallic complex in the case of a diamine compound in a liquid solvent (e.g. 2- propanol) at 15-100°C under usually 1 atm to thereby afford the objective alcohols represented by formula II [e.g. (+)-4-phenylbenzhydrol].
IKARIYA TAKAO
OKUMA TAKESHI
NOYORI RYOJI
SUMITOMO CHEMICAL CO
NIPPON KOKAN KK