Disclosed are complexes and methods of using the complexes as catalysts for addition of amines to unsaturated electrophiles, as well as novel compounds produced by the disclosed complexes and methods. The disclosed methods may utilize the disclosed complexes as catalysts for adding unprotected primary amines and secondary amines to unsaturated electrophiles in an enantioselective manner to produce novel compounds which may include amino substituted succinimide compounds.

Synthesis of organic compounds that has chirality is an important technique in the fields of pharmaceuticals, agrichemicals, health foods and the like. However, raw materials of a catalyst used for the synthesis of such compounds are expensive, and the synthesis needs many steps, so that it is difficult to reduce the cost. Linking a catalyst center to a polymer chain or a resin through an organic group enables to use the catalyst repeatedly and produce a chiral compound at low cost.

The present invention relates to a novel ligand compound represented by Formula 1 and a novel transition metal compound represented by Formula 2, and the novel ligand compound and transition metal compound according to the present invention has high comonomer incorporation effect in the preparation of an olefinic polymer having a low density and a high molecular weight, and thus can be usefully used as a catalyst for a polymerization reaction.

The present disclosure provides a method for efficiently producing and providing compounds having a spirooxindole skeleton, for example compounds having a spirooxindole skeleton and having antitumor activity that inhibit the interaction between Mdm2 protein and p53 protein, or intermediates thereof, using an asymmetric catalyst. Compounds having optically active tricyclic dispiroindole skeletons are obtained through catalytic asymmetric 1,3-dipolar cycloaddition reaction using ketimine as a reaction substrate and using a chiral ligand and a Lewis acid.

The present invention relates to a novel ligand compound represented by Formula 1 and a novel transition metal compound represented by Formula 2, and the novel ligand compound and transition metal compound according to the present invention has high comonomer incorporation effect in the preparation of an olefinic polymer having a low density and a high molecular weight, and thus can be usefully used as a catalyst for a polymerization reaction.

The present invention relates to a novel ligand compound represented by Formula 1 and a novel transition metal compound represented by Formula 2, and the novel ligand compound and transition metal compound according to the present invention has high comonomer incorporation effect in the preparation of an olefinic polymer having a low density and a high molecular weight, and thus can be usefully used as a catalyst for a polymerization reaction.

The present disclosure provides a method for efficiently producing and providing compounds having a spirooxindole skeleton, for example compounds having a spirooxindole skeleton and having antitumor activity that inhibit the interaction between Mdm2 protein and p53 protein, or intermediates thereof, using an asymmetric catalyst. Compounds having optically active tricyclic dispiroindole skeletons are obtained through catalytic asymmetric 1,3-dipolar cycloaddition reaction using ketimine as a reaction substrate and using a chiral ligand and a Lewis acid.

Disclosed are complexes and methods of using the complexes as catalysts for addition of amines to unsaturated electrophiles, as well as novel compounds produced by the disclosed complexes and methods. The disclosed methods may utilize the disclosed complexes as catalysts for adding unprotected primary amines and secondary amines to unsaturated electrophiles in an enantioselective manner to produce novel compounds which may include amino substituted succinimide compounds.

The invention relates to a method of forming an olefin from a first olefin and a second olefin in a metathesis reaction, comprising step (i): (i) reacting the first olefin with the second olefin in the presence of a compound that catalyzes said metathesis reaction such that the molar ratio of said compound to the first or the second olefin is from 1:500 or less, and the conversion of the first or the second olefin to said olefin is at least 50%, characterized in that as compound that catalyzes said metathesis reaction a compound of the following formula is used:

##STR00001## wherein M is Mo or W; R.sup.1 is aryl, heteroaryl, alkyl, or heteroalkyl; optionally substituted; R.sup.2 and R.sup.3 can be the same or different and are hydrogen, alkyl, alkenyl, heteroalkyl, heteroalkenyl, aryl, or heteroaryl; optionally substituted; R.sup.5 is alkyl, alkoxy, heteroalkyl, aryl, heteroaryl, silylalkyl, silyloxy, optionally substituted; and R.sup.4 is a residue R.sup.6X, wherein X=O and R.sup.6 is aryl, optionally substituted; or X=S and R.sup.6 is aryl, optionally substituted; or X=O and R.sup.6 is (R.sup.7, R.sup.8, R.sup.9)Si; wherein R.sup.7, R.sup.8, R.sup.9 are alkyl or phenyl, optionally substituted; or X=O and R.sup.6 is (R.sup.10, R.sup.11, R.sub.12)C, wherein R.sup.10, R.sup.11, R.sup.12 are independently selected from phenyl, alkyl; optionally substituted; and to the catalysts used in the method.

The present disclosure provides compounds, compositions, and methods for preparing alkenyl halides and/or haloalkyl-substituted olefins with Z-selectivity. The methods are particularly useful for preparing alkenyl fluorides such as CF.sub.3-substituted olefins by means of cross-metathesis reactions using halogen-containing molybdenum and tungsten complexes.