PRODUCTION OF OPTICALLY ACTIVE 1,2-DIOLS

• Main Authors: OKANO KAZUYA, IWANE HIROSHI
• Format: Patent
• Language: English
• Published: 11.07.2000
• Edition: 7
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; APPARATUS THEREFOR; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; GENERAL METHODS OF ORGANIC CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; THEIR RELEVANT APPARATUS; TRANSPORTING

PROBLEM TO BE SOLVED: To more simply produce the subject optically active 1,2-diol that is useful as a synthetic intermediate for medicines and agrochemicals or as a ligand for catalyst in high selectivity by the asymmetric hydrogen transfer reduction in the presence of a metal catalyst having a specific ligand. SOLUTION: A diketone represented by formula I [one of R1 and R2 is a (substituted) aromatic hydrocarbon group, an aromatic heterocyclic group or an aliphatic hydrocarbon group; the other is a (substituted) aliphatic hydrocarbon group or R1 and R2 bond to or condense with each other to form a ring], typically 1,2-cyclohexane dione or the like is asymmetrically reduced with a hydrogen donor (for example, an alcohol, formic acid or the like) in the presence of a catalyst prepared by combining a metal compound in the group 8 in the periodic table (for example, a ruthenium compound) with an asymmetric ligand of formula II (R3 and R4 are each a (substituted) alkyl, aryl, aromatic heterocyclic group or R3 and R4 bond to or condense with each other to form a ring; R5 and R6 are each H, a lower alkyl, acyl or the like; and (*) means an asymmetric carbon atom) (for example, having the structure of formula III) to give the objective compound of formula IV.