The present application discloses a 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-based phosphine ligand, an intermediate, a preparation method and uses thereof. The compound of phosphine ligand is a compound having a structure represented by formula I or formula II, or an enantiomer, a raceme, or diastereomer thereof. The phosphine ligand can be prepared via a preparation scheme in which the cheap and easily available 6,6′-dihydroxyl-3,3,3′,3′-tetramethyl-1,1′-spirobiindane is used as a raw material and the compound represented by formula III serves as the key intermediate. The new phosphine ligand developed by the present application can be used in catalytic organic reaction, in particular as a chiral phosphine ligand that is widely used in many asymmetric catalytic reactions including asymmetric hydrogenation and asymmetric allyl alkylation, and thus it has economic practicability and industrial application prospect. ##STR00001##

The present disclosure relates to a ligand compound, a catalyst system for oligomerization, and a method for olefin oligomerization using the same. The catalyst system for oligomerization using the ligand compound according to the present disclosure has excellent catalytic activity, exhibits high selectivity to 1-hexene and 1-octene, and greatly reduces the production of the by-products, thereby enabling efficient preparation of alpha-olefin.

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.)

Provided is a process for producing an optically active hydroxyaldehyde or aminohydroxyaldehyde. The process for producing an optically active hydroxyaldehyde or aminohydroxyaldehyde is characterized by reacting an aldehyde or an imine with a boric acid enol ester in the presence of a copper compound and an optically active bidentate phosphine compound.

The present invention relates to a compound represented by the chemical formula 1, a catalyst system for olefin oligomerization comprising the same, and a method for oligomerizign olefins using the same, and the catalyst system for olefin oligomerization according to the present invention has excellent catalytic activity as well as high selectivity for 1-hexene or 1-octene, thereby enabling more efficient preparation of alpha-olefins.

An organometallic compound represented by Formula 1:

##STR00001##

wherein M.sub.1 and M.sub.2 are each independently a Period 1 transition metal, a Period 2 transition metal, or a Period 3 transition metal in the periodic table of elements; and wherein L.sub.1, L.sub.2, a1, a2, Ar.sub.1, Ar.sub.2, R.sub.1 to R.sub.4, and LK in Formula 1 are as described in the present disclosure.

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.)

An organometallic compound represented by Formula 1

##STR00001## wherein, M.sub.1 to M.sub.4 are each independently a first-row transition metal, a second-row transition metal, or a third-row transition metal; X.sub.1 and X.sub.2 are each independently C(R.sub.5)(R.sub.6), Si(R.sub.5)(R.sub.6), N(R.sub.5), O, S, Se, or Te; W.sub.1 to W.sub.4 are each independently N(R.sub.7)(R.sub.8), P(R.sub.7)(R.sub.8), S(R.sub.7), a C.sub.5-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a; L.sub.1 to L.sub.6 are each independently a C.sub.1-C.sub.30 alkylene group unsubstituted or substituted with at least one R.sub.10a, a C.sub.5-C.sub.60 carbocyclic group unsubstituted or substituted with at least one R.sub.10a, or a C.sub.1-C.sub.60 heterocyclic group unsubstituted or substituted with at least one R.sub.10a, a3 to a6 are each independently an integer from 0 to 3, and R.sub.1 to R.sub.8 and R.sub.10a in Formula 1 are as described herein.

Several dimethylphosphine sulfide- and phosphine-containing compounds have been discovered that chelate copper(I) with high affinity. In certain embodiments, the compounds can be used to quantify copper(I) in complex biological systems. In another embodiment, the compounds can be used for the treatment of copper(I)-related illnesses and conditions. In still other embodiments, the compounds are ratiometric probes.

Processes to produce tunable mixtures of 1-hexene and 1-octene are described. The process includes contacting a mixture of a 1-hexene catalyst and a 1-octene catalyst with ethylene under conditions sufficient to produce a composition that includes a desired amount 1-hexene and 1-octene are described.