Abstract: T-butyl (R)-(-)-4-cyano-3-hydroxybutyrate having an optical purity of 99%ee or higher and a process for producing the same are disclosed, the process comprising cyanogenation of a t-butyl (S)-(-)-4-halogeno-3-hydroxybutyrate obtained by enantioselective hydrogenation of a t-butyl 4-halogenoacetoacetate. Recrystallization of the resulting crude product gives the optically active compound with high optical purity.

Abstract: A process for producing an optically active .gamma.-butyrolactone derivative represented by formula (II): ##STR1## wherein R.sup.1 represents an alkyl group having from 1 to 10 carbon atoms or a substituted or unsubstituted phenyl group; and * indicates an asymmetric carbon atom, is disclosed, comprising enantioselectively hydrogenating a .gamma.-keto acid or an ester thereof represented by formula (I): ##STR2## wherein R.sup.1 and * are as defined above; and R.sup.2 represents a hydrogen atom or a lower alkyl group, in the presence of an optically active ruthenium-phosphine complex. The compounds (I) can be obtained at high optical purity through simple operations and a reduced number of steps.

Abstract: A process for preparing optically active 4-methyl-2-oxetanone which comprises asymmetrically hydrogenating 4-methylene-2-oxetanone in the presence of a ruthenium-optically active phosphine complex. Optically active 4-methyl-2-oxetanone can easily and economically be obtained at high optical purity.

Abstract: Disclosed herein is a process for producing a .gamma.-hydroxyketone (2), which comprises asymmetrically hydrogenating a .gamma.-diketone (1) in the presence of a ruthenium-optically active phosphine complex as a catalyst ##STR1## wherein R.sup.1 and R.sup.2 mean individually an alkyl or phenyl group which may have a substituent group. According to the invention, optically active .gamma.-hydroxyketones useful in synthesizing optically active moiety in, biodegradable polymers, perfumes, intermediates for synthesizing medicines and the like can be efficiently prepared.

Abstract: An alkali metal sulfonate-substituted binaphthyl-phosphine transition metal complex is disclosed, which is represented by formula (I)[M(X).sub.n (Q)(SO.sub.3 A--BINAP)]Y (I)wherein M represents a transition metal atom; SO.sub.3 A--BINAP represents a tertiary phosphine represented by formula (II) ##STR1## in which A represents an alkali metal atom; X represents a chlorine atom, a bromine atom, or an iodine atom;when n is 1, M represents ruthenium, Q represents benzene or p-cymene, and Y represents a chlorine atom, a bromine atom, or an iodine atom;when n is 0 and M is iridium or rhodium, Q represents 1,5-cyclo-octadiene or norbornadiene, and Y represents ClO.sub.4, PF.sub.6 or BF.sub.4 ; and when n is 0 and M is palladium, Q represents .pi.-allyl, and Y represents ClO.sub.4, PF.sub.6, or BF.sub.4.

Abstract: A process for producing an optically active 1-substituted-1,3-propanediol is disclosed, comprising hydrogenating a 3-substituted-3-oxopropanol or 3-substituted-3-oxopropanal in the presence of a ruthenium-phosphine complex represented by formula (I):[RuI(p-cymene)(R.sup.1 BINAP)]I.sub.3 (I)wherein R.sup.1 -BINAP represents an optically active tertiary phosphine represented by formula (II): ##STR1## wherein R.sup.1 represents a phenyl group which may be substituted with a lower alkyl group or a halogen atom at the p-position and/or m-position.

Abstract: Novel 2,2'-bis(dicyclopentylphosphino)-1,1'-binaphthyl represented by formula (I): ##STR1## and a transition metal complex using the same as a ligand, are disclosed. The transition metal complex is industrially excellent as a catalyst for various asymmetric synthesis reactions.

Abstract: A process for preparing optically active 4-methyl-2-oxetanone which comprises asymmetrically hydrogenating 4-methylene-2-oxetanone in the presence of a ruthenium-optically active phosphine complex. Optically active 4-methyl-2-oxetanone can easily and economically be obtained at high optical purity.

Abstract: A process for preparing a 4-acyloxyazetidinone or a derivative thereof represented by formula (IV): ##STR1## wherein R.sup.1 represents a hydrogen atom, a lower alkyl group, a hydroxyethyl group, or a protected hydroxyethyl group; R.sup.3 represents an alkyl group having from 1 to 10 carbon atoms which may be substituted with a halogen atom, a cyano group, a lower alkoxy group or a phenyl group, or a substituted or unsubstituted phenyl group, provided that the .alpha.-positioned carbon atom of said alkyl group should not have more than two halogen atoms; and R.sup.4 represents a hydrogen atom, a lower alkyl group, or a lower alkoxycarbonyl group, which is useful as an intermediate for penem antibiotics is disclosed, comprising reacting azetidinone or a derivative thereof represented by formula (II): ##STR2## wherein R.sup.1 is as defined above, and R.sup.2 represents a hydrogen atom, a lower alkyl group, a lower alkoxycarbonyl group, or a carboxyl group,with a carboxylic acid represented by formula (III):R.

Abstract: A (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative and a process of producing the (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative which comprises the step of enantioselectively hydrogenating an (S)-5,6-dihydroxy-3-oxohexanoic acid derivative with a specific ruthenium-optically active phosphine complex represented as a catalyst are disclosed. The (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative which is a useful compound capable of being easily converted into a lactone moiety, which is the active part of an inhibitor on HMG-CoA reductase, can be easily and efficiently obtained under a mild reaction condition with a high selectivity for the syn-diol form.

Abstract: A ruthenium-phosphine complex is disclosed, represented by formula (I):[RuI(p-cymene)(R.sup.1 -BINAP)]I.sub.3 (I)where R.sup.1 -BINAP represents a tertiary phosphine represented by formula (II): ##STR1## wherein R.sup.1 represents a phenyl group which may be substituted with a lower alkyl group or a halogen atom at the p-position and/or m-position. A process for producing an optically active 1-substituted-1,3-propanediol is also disclosed, comprising hydrogenating a 3-substituted-3-oxopropanol or 3-substituted-3-oxopropanal in the presence of the ruthenium-phosphine complex of formula (I).

Abstract: An alkali metal sulfonate-substituted binaphthyl-phosphine transition metal complex is disclosed, which is represented by formula (I)[M(X).sub.n (Q)(SO.sub.3 A-BINAP)]Y (I)whereinM represents a transition metal atom;SO.sub.3 A-BINAP represents a tertiary phosphine represented by formula (II) ##STR1## in which A represents an alkali metal atom; X represents a chlorine atom, a bromine atom, or an iodine atom;when n is 1, M represents ruthenium, Q represents benzene or p-cymene, and Y represents a chlorine atom, a bromine atom, or an iodine atom;when n is 0 and M is iridium or rhodium, Q represents 1,5-cyclo-octadiene or norbornadiene, and Y represents ClO.sub.4, PF.sub.6 or BF.sub.4 ; andwhen n is 0 and M is palladium, Q represents .pi.-allyl, and Y represents ClO.sub.4, PF.sub.6, or BF.sub.4.

Abstract: A phosphine compound represented by formula (I): ##STR1## wherein Ph represents a phenyl group; and R represents a lower alkyl group or --OR.sup.1, wherein R.sup.1 represents a hydrogen atom, a cycloalkyl group having from 5 to 7 carbon atoms, or an alkyl group having from 1 to 6 carbon atoms which may be substituted with a halogen atom, a lower alkoxy group, a lower alkoxy group-substituted lower alkoxy group, or a phenyl group, and a transition metal complex using the phosphine compound (I) as a ligand are disclosed. The transition metal complex, when used as a catalyst for various enantioselective synthesis reactions, e.g., enantioselective silylation reaction, provides a desired product in high yield at high optical purity. The absolute configuration of the product can be arbitrarily selected by selecting the optical isomer of the ligand in the transition metal complex catalyst.

Abstract: A 2,2'-bis[di-(3,5-dialkylphenyl)phosphino]-1,1'-binaphthyl represented by formula (I): ##STR1## wherein R represents a lower alkyl group, is disclosed. A transition metal complex comprising a transition metal and a 2,2'-bis[di(3,5-dialkylphenyl)phosphino]-1,1'-binaphthyl represented by formula (I) as a ligand is also disclosed.

Abstract: A process for producing an .alpha.-hydroxyketone represented by formula (I): ##STR1## wherein R.sup.1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or an alkoxycarbonyl group; and R.sup.2 and R.sup.3 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group, provided that they do not simultaneously represent a hydrogen atom; or a pair of R.sup.1 and R.sup.2, a pair of R.sup.1 and R.sup.3, or a pair of R.sup.2 and R.sup.3 is taken together to form a ring; and the pair of R.sup.1 and R.sup.2 and the pair of R.sup.2 and R.sup.3 may form a ring simultaneously, is disclosed, comprising reacting a compound represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are as defined above, with an oxidizing agent in the presence of a ruthenium compound and water. .alpha.-Hydroxyketones useful as physiologically active substances are produced with good selectivity and in high yield.

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: 2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl represented by formula (I). ##STR1## is disclosed. A transition metal complex containing the same, a process for producing 2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl, and a process for producing 2,2'-bis(diphenylphosphinyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl are also disclosed.

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 represented by the formula [Ru(B).sub.2 (L)].sub.m wherein B is Cl, Br or l, m is a positive integer, and L is 1,5-cyclooctadiene, norbornadiene, cycloheptatriene, cyclooctatetraene or benzene which may or may not have a lower alkyl group as a substituent, as a catalyst.

Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R.sup.2 -BINAP represents a teritary phosphine compound represented by formula (II): ##STR2## wherein R.sup.2 represents a hydrogen atom, a methyl group, a methoxy group, or a t-butyl group; X represents a halogen atom; and R and R.sup.1, which may be the same or different, each represent a phenyl group or a substituted phenyl group, and a ruthenium-phosphine complex represented by formula (III): ##STR3## wherein R and R.sup.1 are as defined above; and dma represents N,N-dimethylacetamide, which is an intermediate for synthesizing the ruthenium-phosphine complex of formula (I), are disclosed. The complex of formula (I) is useful as a catalyst for general syntheses with its ligand being an optically inactive compound or for asymmetric syntheses with its ligand being an optically active compound and, also, can be prepared at a low cost.

Abstract: A process for producing a 4-acetoxyazetidinone represented by formula (I): ##STR1## wherein Z represents a hydrogen atom, a lower alkyl group, or a protected or unprotected hydroxyethyl group; and W represents a hydrogen atom, a lower alkyl group, or a group of --COOR.sup.1, wherein R.sup.1 represents a lower alkyl group, is disclosed, which comprises reacting an azetidinone represented by formula (II): ##STR2## wherein Z is as defined above; and Y represents a hydrogen atom, carboxyl group, a lower alkyl group, or a group of --COOR.sup.1, wherein R.sup.1 represents a lower alkyl group, with acetic acid and an oxidizing agent in the presence of, as a catalyst, an anhydrous or hydrous osmium compound represented by OsX.sub.3, wherein X represents a chlorine atom, a bromine atom, or an iodine atom.