Abstract: An iridium-optically active phosphine complex represented by formula (I):[H.sub.2 Ir(L.sup.1)(L.sup.2)]Y (I)wherein L.sup.1 represents an optically active phosphine compound represented by formula (II): ##STR1## wherein Ar represents a phenyl group or a p- and/or m-lower alkyl-substituted phenyl group, or formula (III): ##STR2## L.sup.2 represents a tertiary phosphine compound represented by formula (IV): ##STR3## wherein Z represents a lower alkoxy group or a di-lower alkylamino group; and A represents an integer of from 1 to 3; Y represents BF.sub.4, PF.sub.6, ClO.sub.4, or BPh.sub.4, wherein Ph represents a phenyl group, and a process for producing an optically active alcohol using the above complex as an enantioselective catalyst are disclosed. The complex exhibits excellent catalytic activity to give high enantioselective yields in enantioselective synthesis, particularly enantioselective hydrogenation.

Abstract: A process for preparing optically active 3-hydroxypyrrolidine derivatives useful as intermediates represented by formula (III): ##STR1## wherein Q represents a substituted or unsubstituted phenyl group; and * indicates an asymmetric carbon atom, comprising reacting an optically active 4-halo-3-hydroxybutane derivative represented by formula (I): ##STR2## wherein * is as defined above; R.sup.1 represents a lower alkyl group or a substituted or unsubstituted phenyl group; and X represents a halogen atom, with a benzylamine derivative represented by formula (II):H.sub.2 NCH.sub.2 Q (II)wherein Q is as defined above, is disclosed. The starting compound (I) is easily available through chemical synthesis. Any complicated procedure or use of an expensive reagent is not required.

Abstract: A process for production of an optically active isomer of 2-(tetrahydropyran-2-yloxy)-1-propanol represented by formula (I): ##STR1## is disclosed, which comprises reacting an optically active isomer of a 1-acyloxy-2-propanol represented by formula (II): ##STR2## wherein R is a substituted or unsubstituted aryl group, with 3,4-dihydro-2H-pyran to obtain an optically active isomer of a 1-acyloxy-2-(tetrahydropyran-2-yloxy)propane represented by formula (III): ##STR3## wherein R is as defined above, and hydrolyzing the compound (III) to eliminate the acyl group. The optically active isomer of 2-(tetrahydropyran-2-yloxy)-1-propanol represented by formula (I) is an intermediate for synthesis of pyridobenzoxazine derivatives useful as a synthetic antibacterial agent, particularly an optically active isomer of ofloxacin.

Abstract: A process for preparing an optically active ketone represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 5 carbon atoms; and n represents 1 or 2,which comprises asymmetrically hydrogenating an .alpha., .beta.-unsaturated ketone represented by formula (II): ##STR2## wherein R.sup.1 and n are as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst. An optically active ketone having a high optical purity can be prepared.

Abstract: A simplified process for preparing 4-acetoxyazetidinones of formula (I): ##STR1## wherein Z is a hydrogen atom, a lower alkyl group or a hydroxyethyl group which may or may not be protected is disclosed. According to the invention, azetidinones of formula (II): ##STR2## wherein Z has the same meaning as defined above and Y is a hydrogen atom or a carboxyl group is reacted with acetic acid and an oxidizing agent in the presence of a ruthenium compound as a catalyst.

Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a carbonyl compound in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.

Abstract: 2,2'-Bis[di-(m-tolyl)phosphino]-1,1'-binaphthyl represented by formula (I) is disclosed. ##STR1## The compound of formula (I) is capable of forming a complex with a metal, e.g., ruthenium, rhodium, and palladium, which is extremely important and industrially excellent as a catalyst for various asymmetric synthesis reactions.

Abstract: A ruthenium-phosphine complex represented by formula (I)[RuX.sub.l (L).sub.m (R-BINAP)]Y.sub.n (I)wherein R-BINAP represents a tertiary phosphine represented by formula (II): ##STR1## wherein R represents a hydrogen atom or a methyl group; X represents a halogen atom; L represents substituted or unsubstituted benzene or acetonitrile; Y represents a halogen atom, CLO.sub.4, PF.sub.6, BPh.sub.4 (wherein Ph represents a phenyl group) or BF.sub.4 ; when L is substituted or unsubstituted benzene, l represents 1, m represents 1, and n represents 1; and whe L is acetonitrile, when l is 1, then m represents 2, and n represents 1, and when l is 0, the m represents 4, and n represent 2. The complex exhibits excellent catalytic activity in asymmetric reactions to provide a product of high optical purity. The complex can be produced at low cost.

Abstract: A process for preparing an optically active 6-t-butoxy-3,5-dihydroxyhexanoic ester represented by formula: ##STR1## wherein t-Bu represents a t-butyl group; and R.sup.4 represents a lower alkyl group, which is useful as a precursor of a lactone moiety of campactin, mevinolin or analogues thereof is disclosed, comprising asymmetrically hydrogenating a 4-t-butoxyacetoacetic ester in the presence of a ruthenium-optically active phosphine complex to obtain an optically active 4-t-butyoxy-3-hydroxybutanoic ester, reacting the ester with a lithium enolate of an acetic ester to obtain an optically active 6-t-butyoxy-5-hydroxy-3-oxohexanoic ester, and asymmetrically hydrogenating the resulting ester in the presence of a ruthenium-optically active phosphine complex as a catalyst. The desired product can be obtained in good yield at high stereoselectivity.

Abstract: A process for preparing an .alpha.-hydroxycarboxylate represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a lower alkyl group, a phenyl group or a cycloalkyl group, or R.sup.1 and R.sup.2 are bonded to each other to form a five- to seven-membered cycloalkenyl or bicycloalkenyl ring which may be substituted with a lower alkyl group; and R.sup.3 represents a lower alkyl group,which comprises reacting an olefin compound represented by formula (II): ##STR2## wherein R.sup.1 ' represents a hydrogen atom or a lower alkyl group; and R.sup.2 ' represents a lower alkyl group, a phenyl group or a cycloalkyl group, or R.sup.1 ' and R.sup.2 ' are bonded to each other to form a five- to seven-membered cycloalkyl or bicycloalkyl ring which may be substituted with a lower alkyl group,with a glyoxylate represented by formula (III): ##STR3## wherein R.sup.

Abstract: A process for producing an optically active carboxylic acid represented by formula (I): ##STR1## wherein R.sup.1, and R.sup.2, and R.sup.3 each represents a hydrogen atom, an alkyl group, an alkenyl group, or a phenyl or naphthyl group which may have a substituent, provided that all of R.sup.1, R.sup.2, and R.sup.3 are not simultaneously a hydrogen atom; when R.sup.1 and R.sup.2 are simultaneously a hydrogen atom, then R.sup.3 is not a methyl group; and that when R.sup.3 is a hydrogen atom, then R.sup.1 and R.sup.2 are each a group other then a hydrogen atom,is disclosed, comprising asymmetrically hydrogenating an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are the same as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst.

Abstract: A process for producing an optically active alcohol represented by formula (I): ##STR1## wherein R.sub.1 is an alkyl group having from 2 to 11 carbon atoms, an alkenyl group having from 3 to 11 carbon atoms, an alkadienyl group having from 6 to 11 carbon atoms, a cyclohexyl group, an cyclohexylmethyl group, or a cyclohexylethyl group, provided that the olefin in the alkenyl group or alkadienyl group is not conjugated to the olefin at the 2-position thereof; and * means an asymmetric carbon atom,is disclosed, comprising subjecting an olefinic alcohol represented by formula (II): ##STR2## wherein R.sub.1 is the same as defined above to asymmetric hydrogenation in the presence of, as a catalyst, a ruthenium-optically active phosphine complex.According to the process of the invention, the desired optically active alcohols which are useful not only as intermediates for the manufacture of perfumes and vitamin E but also as liquid crystal materials can be produced with high optical purities.

Abstract: A ruthenium-phosphine complex is disclosed, which is represented by formula (I):[Ru(R-BINAP)MCl.sub.k ].sub.l X.sub.m (I)wherein R-BINAP represents a tertiary phosphine represented by formula (II): ##STR1## wherein R represents hydrogen atom or methyl group; M represents Zn, Al, Ti, or Sn; X represents N(C.sub.2 H.sub.5).sub.3 or CH.sub.3 CO.sub.2 ; in the case that X represents N(C.sub.2 H.sub.5).sub.3, l is 2 and m is 1, and when M represents Zn, then k is 4, when M represents Al, then k is 5, and when M represents Ti or Sn, then k is 6; and in the case that X represents CH.sub.3 CO.sub.2, l is 1 and m is 2, and when M represents Zn, then k is 2, when M represents Al, then k is 3, and when M represents Ti or Sn, then k is 4.

Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a .beta.-keto acid derivative in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.

Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.

Abstract: A process for preparing optically active threonine is disclosed, which comprises asymmetrically hydrogenating a 2-N-acylaminoacetoacetic ester represented by formula (I): ##STR1## wherein R.sup.1 represents a lower alkyl group, a phenyl group, a phenyl group substituted with a lower alkyl group or a lower alkoxy group, a benzyl group, or a benzyl group substituted with a lower alkyl group or a lower alkoxy group; R.sup.2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a phenyl group, a phenyl group substituted with a lower alkyl group or a lower alkoxy group, a benzyloxy group, or a benzyloxy group substituted with a lower alkyl group or a lower alkoxy group, in the presence of a ruthenium-optically active phosphine complex as a catalyst to obtain an optically active threonine derivative represented by formula (II): ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, and then hydrolyzing the compound of formula (II).

Abstract: A process for preparing carnitine which comprises asymmetrically hydrogenating a .gamma.-halogeno-.beta.-keto ester represented by formula (I): ##STR1## wherein X represents a chlorine atom or a bromine atom; and R represents a lower alkyl group, in the presence of a ruthenium-optically active phosphine complex represented by formula (II), (III) or (IV):Ru.sub.2 Cl.sub.4 (L).sub.2 (C.sub.2 H.sub.5).sub.3 N (II)Ru(OCOR.sup.2).sub.2 (L) (IV)RuX.sub.2 (L) (V)wherein L represents 2,2'-bis(di-p-R.sup.1 -phenylphosphino)- 1,1'-binaphthyl of formula (III): ##STR2## wherein R.sup.1 represents a hydrogen atom, a methyl group, or a t-butyl group;R.sup.2 represents a lower alkyl group or a trifluoromethyl group; and X is as defined above,as a catalyst at a temperature of from 70.degree. to 150.degree. C.

Abstract: A process for preparing an N-acyltetrahydroisoquinoline represented by formula (II) ##STR1## wherein A represents a phenylene ring substituted with a hydroxyl group, a lower alkoxy group, an acetoxy group, or a benzyloxy group; R represents a hydrogen atom, a lower alkyl group, or a phenyl group; and X represents a hydrogen atoms, a phenyl group, or a phenyl group substituted with a hydroxyl group, a lower alkoxy group, or an acetoxy group, which comprises asymmetrically hydrogenating an N-acyl-1-methylenetetrahydroisoquinoline or N-acyl-1-benzylidenetetrahydroisoquinoline represented by formula (I) ##STR2## wherein A, R, and X are as defined above, in the presence of an optically active ruthenium-phosphine complex as a catalyst. The process exclusively and efficiently provides a useful isomer of the N-acyltetrahydroisoquinoline of high purity which is useful as an intermediate for synthesizing isoquinoline type alkaloids as pharmaceuticals without involving optical resolution of a racemate.

Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, a methyl group, or a methoxy group; and R.sup.2 represents a lower alkyl group, a halogenated lower alkyl group, a phenyl group, or a phenyl group substituted with a lower alkyl group. The complex is inexpensive and exhibits excellent performance as a catalyst for various organic syntheses, particularly for asymmetric hydrogenation.

Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R represents a hydrogen atom, a methyl group, or a methoxy group; and X represents ClO.sub.4, BF.sub.4, or PF.sub.6. The ruthenium-phosphine complex is inexpensive and exhibits excellent performance as a catalyst for various organic syntheses, particularly for asymmetric hydrogenation.