Process for producing optically active diaminohexanone derivative

A process for producing a (2S,5S)-2,5-diamino-1, 6-diphenyl-3-hexanone derivative represented by the formula (1):

• ##STR18## wherein R.sup.1 means a lower alkylcarbonyl group, a halogen-substituted lower alkylcarbonyl group, an arylcarbonyl group or a lower alkoxycarbonyl group, and R.sup.2 and R.sup.3 are identical with or different from each other and denote individually an aryl group or an alkoxy-substituted aryl group, which comprises subjecting a (2S)-2,5-diamino-1,6-diphenyl-4-hexen-3-one derivative represented by the formula (2):
• ##STR19## wherein R.sup.1, R.sup.2 and R.sup.3 have the same meaning as defined above, to a hydrogenation reaction in the presence of a transition metal-containing catalyst, wherein said transition metal-containing catalyst is either a mononuclear complex represented by the formula (3):
• M(L.sub.n)(Y.sub.p)(X.sub.q) (3)
• wherein M is ruthenium, rhodium, palladium or iridium, L denotes an organophosphorus compound represented by the formula (6):
• (R.sup.5).sub.2 P-A-P(R.sup.3).sub.2 ( 6)
• wherein R.sup.5 means a lower alkyl group, a phenyl group or a tolyl group, and A denotes the formula (7):
• (R.sup.6)CH(CH.sub.2).sub.m CH(R.sup.7) (7)
• in which R.sup.6 and R.sup.7 mean individually a lower alkyl group, or R.sup.6 and R.sup.7 are bonded to each other to form a ring, and m stands for a number of 0-8, or the formula (8):
• ##STR20## wherein R.sup.10 means a methyl group, and R.sup.8 and R.sup.9 denote individually a hydrogen atom, a halogen atom or a lower alkyl group, with the proviso that R.sup.9 and R.sup.10 may form together a carbocyclic or aryl ring,
• Y stands for cyclooctadiene, norbornadiene, p-cymene, acetonitrile, ethylene, pyridine, acetic acid or benzene, X is a halogen ion, sulfonate ion, acetate ion, nitrile ion, ClO.sub.4, BF.sub.4 or PF.sub.4, or X and Y may form together a .beta.-diketonate, n stands for a number of 1-3, and p and q are individually a number of 0-2, or a binuclear complex represented by the formula (4):
• M.sub.2 (L.sub.2n)(Y.sub.2p)(X.sub.2q) (4)
• wherein M, L, X, Y, n, p and q have the same meaning as defined above.