There is provided a novel optically active bisphosphinomethane useful as a ligand for an asymmetric catalyst, excellent in oxidation resistance in air, and easy in handling. There is also provided a transition metal complex using the optically active bisphosphinoraethane having excellent asymmetric catalytic ability as a ligand. The optically active bisphosphinomethane is represented by the general formula (1), and the transition metal complex has the optically active bisphosphinomethane as a ligand. ##STR00001##
(In the formula, R.sup.1 represents an adamantyl group; R.sup.2 represents a branched alkyl group having 3 or more carbon atoms; and * represents an asymmetric center on a phosphorus atom.)

The purpose of the present invention is to provide: a ligand that is useful in a catalytic organic synthetic reaction; a method for producing said ligand; and a metal complex that is useful as a catalyst in an organic synthetic reaction. The present invention provides a compound represented by general formula (1.sup.A), a method for producing said compound, and a metal complex including said compound as a ligand. (In the formula, H, N, P, S, L, R.sup.1, R.sup.2, R.sup.3, Q.sup.1, and Q.sup.2 have the meaning as defined in the Description.)

##STR00001##

There is provided a novel optically active bisphosphinomethane useful as a ligand for an asymmetric catalyst, excellent in oxidation resistance in air, and easy in handling. There is also provided a transition metal complex using the optically active bisphosphinoraethane having excellent asymmetric catalytic ability as a ligand. The optically active bisphosphinomethane is represented by the general formula (1), and the transition metal complex has the optically active bisphosphinomethane as a ligand.

##STR00001##

(In the formula, R.sup.1 represents an adamantyl group; R.sup.2 represents a branched alkyl group having 3 or more carbon atoms; and * represents an asymmetric center on a phosphorus atom.)

The present invention refers to a process for the preparation of a mono(acyl)phosphine of the general formula (I) and/or a bis(acyl)phosphine of the general formula (II), wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are the same or different and are independently selected from H, halogen, linear or branched C.sub.1-C.sub.20-alkyl, linear or branched C.sub.2-C.sub.8-alkenyl, C.sub.1-C.sub.8-alkoxy, C.sub.2-C.sub.8-alkenyloxy, C.sub.3-C.sub.8-cycloalkyl, C.sub.6-C.sub.12-aryl, C.sub.3-C.sub.8-cycloalkoxy, C.sub.7-C.sub.12-arylalkoxy, C.sub.9-C.sub.15-alkenylarylalkoxy, nitro-, C.sub.6-C.sub.12-arylsulfonyl, 4-alkylaryl-sulfonyl, C.sub.1-C.sub.20-alkylcarboxy, C.sub.1-C.sub.8-alkoxycarbonyl, SR.sub.14, NIIR.sub.14 or NR.sub.14R.sub.15 with R.sub.14 and R.sub.15 being independently selected from H, linear or branched C.sub.1-C.sub.20-alkyl, linear or branched C.sub.2-C.sub.8-alkenyl and C.sub.3-C.sub.8-cycloalkyl, and an O-, S- or N-containing 5-or 6-membered heterocyclic ring; R.sub.6 is H or R.sub.6 is replaced by an alkaline earth metal cation or a mixed alkali metal/alkaline earth metal cation; Formula (II) wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 are the same or different and are independently selected from H, halogen, linear or branched C.sub.1-C.sub.20-alkyl, linear or branched C.sub.2-C.sub.8-alkenyl, C.sub.1-C.sub.8-alkoxy, C.sub.2-C.sub.8-alkenyloxy, C.sub.3-C.sub.8-cycloalkyl, C.sub.6-C.sub.12-aryl, C.sub.3-C.sub.8-cycloalkoxy, C.sub.7-C.sub.12-arylalkoxy, C.sub.9-C.sub.15-alkenylarylalkoxy, nitro-, C.sub.6-C.sub.12-arylsulfonyl, 4-alkylarylsulfonyl, C.sub.1-C.sub.20-alkylcarboxy, C.sub.1-C.sub.8-alkoxycarbonyl, SR.sub.14, NHR.sub.14 or .sub.NR.sub.14R.sub.15 with R.sub.14 and R.sub.15 being independently selected from H, linear or branched C.sub.1-C.sub.20-alkyl, linear or branched C.sub.2-C.sub.8-alkenyl and C.sub.3-C.sub.8-cycloalkyl, and an O-, S- or N- containing 5- or 6-membered heterocyclic ring; as well as the mono(acyl)phosphine and/or bis(acyl)phosphine obtained by the process.

##STR00001##

The purpose of the present invention is to provide an N,N-bis(2-dialkylphosphinoethyl)amine-borane complex which is a ruthenium complex that exhibits excellent catalytic activity in a hydrogenation reaction, etc., and a production method therefor, and a method for efficiently producing a ruthenium complex containing N,N-bis(2-dialkylphosphinoethyl)amine as a ligand. The present invention is capable of efficiently producing an amine-borane complex (3) by reacting an oxazolidinone compound (1) with a dialkylphosphine-borane compound (2) in the presence of a base. The present invention is also capable of efficiently producing a ruthenium complex (5) by reacting the amine-borane complex (3) with a ruthenium compound (4) in the presence of an amine. ##STR00001##
(In the formula, a solid line, a dashed line, B, C, H, L.sup.1-L.sup.3, LG, n, N, O, P, Ru, X, and R.sup.1-R.sup.10 are as defined in the description.)

The purpose of the present invention is to provide an N,N-bis(2-dialkylphosphinoethyl)amine-borane complex which is a ruthenium complex that exhibits excellent catalytic activity in a hydrogenation reaction, etc., and a production method therefor, and a method for efficiently producing a ruthenium complex containing N,N-bis(2-dialkylphosphinoethyl)amine as a ligand. The present invention is capable of efficiently producing an amine-borane complex (3) by reacting an oxazolidinone compound (1) with a dialkylphosphine-borane compound (2) in the presence of a base. The present invention is also capable of efficiently producing a ruthenium complex (5) by reacting the amine-borane complex (3) with a ruthenium compound (4) in the presence of an amine.

##STR00001##

(In the formula, a solid line, a dashed line, B, C, H, L.sup.1-L.sup.3, LG, n, N, O, P, Ru, X, and R.sup.1-R.sup.10 are as defined in the description.)