Claims
- 1. 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.
- 2. A process as in claim 1, wherein the organophosphorus compound is 2,3-bis (diphenylphosphino)butane, 2,2'-bis(diphenyl)-1,1'-dinaphthyl or 2,2'-bis(ditolyphosphino)-1,1'-dinaphthyl.
- 3. A process as in claim 1, wherein the mononuclear complex is selected from the group consisting of [M(L)(C.sub.2 H.sub.4)Cl], [M(L)(C.sub.2 H.sub.4)Br], [M(L)(C.sub.2 H.sub.4)F], [M(L)(C.sub.2 H.sub.4)I], [M(L)(C.sub.2 H.sub.4)CN], [M(L)(cod)]Cl, [M(L)(cod)]BF.sub.4, [M(L)(cod)]PF.sub.6, [M(L)(nbd)]ClO.sub.4, [M(L)(acac)], [M(L)(pyridime)]Cl, and [M(L)(nbd)CH.sub.3 COO]
- wherein cod means cyclooctradiene, nbd denotes norbornadiene, and acac stands for acetylacetone.
- 4. A process as in claim 1, wherein the organophosphorus compound is an optically active organophosphorus compound represented by the formula (19): ##STR21## wherein R.sup.11 means a phenyl group which may have a substituent group, R.sup.10 is 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 ring.
- 5. A process as in claim 4, wherein the optically active organophosphorus compound is the compound represented by the formula (22): ##STR22## wherein R.sup.12 means a phenyl group which may have a substituent group.
- 6. A process as in claim 5, wherein R.sup.12 is a phenyl group or p-tolyl group.
- 7. A process as in claim 1, wherein the organophosphorus compound is an optically active organophosphorus compound which has asymmetry and is represented by the formula (20) or (21): ##STR23##
- 8. A process as in claim 1, wherein the transition metal-containing catalyst is selected from the group consisting of
- [Rh(cod)(S)-CHIRAPHOS]ClO.sub.4,
- [Rh(cod)(R) -TolBINAP]ClO.sub.4,
- [Ru.sub.2 Cl.sub.4 ((R)-BINAP).sub.2 ](NEt.sub.3),
- [Ru.sub.2 Cl.sub.4 ((S)-BINAP).sub.2 ](NEt.sub.3),
- [Ru(OAc).sub.2 (S)-TolBINAP] and
- [RuI(p-cymene)(R)-TolBINAP]I
- wherein cod means cyclooctadiene, Et is ethyl group, Ac is acetyl group, CHIRAPHOS means an optically active organophosphorus compound represented by the formula (20): ##STR24## TolBINAP means an optically active organophosphorus compound represented by the formula (22): ##STR25## wherein R.sup.12 is p-tolyl group, and BINAP means an optically active organophosphorus compound represented by said formula (22) wherein R.sup.12 is a phenyl group.
- 9. A process as in claim 1, wherein the transition metal-containing catalyst is obtained from [Rh(cod).sub.2 ]ClO.sub.4 wherein cod means cyclooctadiene and an organophosphorus compound selected from the group consisting of
- (2S,3S)-Bis(diphenylphosphino)butane,
- (2R,3R)-Bis(diphenylphosphino)butane,
- (R)-TolBINAP and (S)-TolBINAP
- wherein TolBINAP means an optically active organophosphorus compound represented by the formula (22): ##STR26## wherein R.sup.12 is p-tolyl group.
- 10. A process as in claim 1, wherein the transition metal-containing catalyst is selected from the group consisting of
- Ru(OAc).sub.2 [(S)-TolBINAP],
- Ru(OAc).sub.2 [(R)-BINAP],
- [RuI(p-cymene)((S)-TolBINAP)]I and
- [RuI(p-cymene)((R)-TolBINAP)]I
- wherein Ac is an acetyl group, TolBINAP means an optically active organophosphorus compound represented by the formula (22): ##STR27## wherein R.sup.12 is p-tolyl group, and BINAP means an optically active organophosphorus compound represented by said formula (22) wherein R.sup.12 is a phenyl group.
Priority Claims (1)
Number |
Date |
Country |
Kind |
6-47182 |
Mar 1994 |
JPX |
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Parent Case Info
This is a Division of application Ser. No. 08/229,678, filed on Apr. 19, 1994, now U.S. Pat. No. 5,523,458.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5523458 |
Yamasaki et al. |
Jun 1996 |
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Divisions (1)
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Number |
Date |
Country |
Parent |
229678 |
Apr 1994 |
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