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 herein are dual catalyst compositions containing an unbridged metallocene compound, a bridged metallocene compound, a chemically-treated solid oxide, and an optional co-catalyst. These catalyst compositions can be used for the oligomerization of propylene to produce an oligomer product. For example, a heavy propylene oligomer can be recovered from the oligomer product, and the heavy propylene oligomer can be characterized by a high flash point and viscosity index, and a low pour point.

A preparation method for L-nicotine involves multiple steps. The resulting L-nicotine can have an optical purity of more than 99.9%, much higher than that of similar products in the current market. The total yield of synthesis reaches 50-60%.

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 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 herein are dual catalyst compositions containing an unbridged metallocene compound, a bridged metallocene compound, a chemically-treated solid oxide, and an optional co-catalyst. These catalyst compositions can be used for the oligomerization of propylene to produce an oligomer product. For example, a heavy propylene oligomer can be recovered from the oligomer product, and the heavy propylene oligomer can be characterized by a high flash point and viscosity index, and a low pour point.

Disclosed herein are dual catalyst compositions containing an unbridged metallocene compound, a bridged metallocene compound, a chemically-treated solid oxide, and an optional co-catalyst. These catalyst compositions can be used for the oligomerization of propylene to produce an oligomer product. For example, a heavy propylene oligomer can be recovered from the oligomer product, and the heavy propylene oligomer can be characterized by a high flash point and viscosity index, and a low pour point.

The present invention provides a method of efficiently producing an optically active 6-(3-aminopiperidin-1-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine derivative. The optically active piperidine-3-carboxamide or a derivative thereof, which is obtained by subjecting 1,4,5,6-tetrahydropyridine-3-carboxamide or a derivative thereof to an asymmetric reduction in the presence of a catalyst, is used as an intermediate.

Disclosed herein are dual catalyst compositions containing an unbridged metallocene compound, a bridged metallocene compound, a chemically-treated solid oxide, and an optional co-catalyst. These catalyst compositions can be used for the oligomerization of propylene to produce an oligomer product. For example, a heavy propylene oligomer can be recovered from the oligomer product, and the heavy propylene oligomer can be characterized by a high flash point and viscosity index, and a low pour point.

The present invention provides a method of efficiently producing an optically active 6-(3-aminopiperidin-1-yl)-2,4-dioxo -1,2,3,4-tetrahydropyrimidine derivative. The optically active piperidine-3-carboxamide or a derivative thereof, which is obtained by subjecting 1,4,5,6-tetrahydropyridine -3-carboxamide or a derivative thereof to an asymmetric reduction in the presence of a catalyst, is used as an intermediate.