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.

Process comprising the process steps of:

a) initially charging a pentenoic ester,
b) adding a ligand of structure 1 or 2:

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and a compound comprising a metal atom selected from: Rh, Ru, Co, Ir,
c) supplying H.sub.2 and CO,
d) heating the reaction mixture to convert the pentenoic ester to 5-formylpentanoic esters.

This disclosure relates to CO.sub.2-philic crosslinked polyethylene glycol membranes useful for natural gas purification processes. Also provided are methods of using the membranes to remove CO.sub.2 and H.sub.2S from natural gas.

The metal-catalyzed alkoxycarbonylation of a lactone is a method of alkoxycarbonylating a -lactone, specifically 3-ethylidene-6-vinyltetrahydro-2H-pyran-2-one. The method includes combining the -lactone with an alcohol in an organic solvent in the presence of a catalyst system that includes palladium or a salt thereof to form a reaction mixture, which is heated to 110-130 C. at a pressure of 20-50 bar for between 3-5 hours under flow of carbon monoxide gas. The product of the reaction is a substituted 2-octendioate diester. The alcohol may be methyl alcohol, n-butyl alcohol, 2-ethylhexanol, isobutyl alcohol, isopropyl alcohol, benzyl alcohol, or phenol. The solvent may be toluene, acetonitrile, or tetrahydrofuran. The method may include adding an acid to the reaction mixture, which may be dilute (about 5 mol %) sulfuric or p-toluenesulfonic acid. The catalyst system may also include a phosphine ligand.

The present invention provides methods of preparing Praziquantel, in particular (R)-Praziquantel and analogues thereof in a stereoselective manner. One method involves asymmetric hydrogenation of the following intermediate compound

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and subsequent cyclization.

The present invention relates to a new process for the production of D-sorbitol.

Catalytic process for preparing an ,-ethylenically unsaturated carboxylic acid salt, comprising reacting an alkene and carbon dioxide in the presence of a carboxylation catalyst and releasing the ,-ethylenically unsaturated carboxylic acid salt with a base, the carboxylation catalyst being a transition metal complex, which comprises a structurally constrained bidentate P,X ligand, wherein X is selected from the group consisting of P, N, O, and carbene, the P and X atom are separated by 2 to 4 bridging atoms, and wherein the bridging atoms are part of at least one 5- to 7-membered cyclic substructure. A further catalytic processes for preparing ,ethylenically unsaturated carboxylic acid derivatives from CO.sub.2 and an alkene is provided.

In one aspect, methods for the facile synthesis of cationic cobalt complexes for asymmetric hydrogenation of alkenes are provided. Synthetic methods described herein, in some embodiments, provide Co(I) precatalysts on a time scale and yield permitting catalytic evaluation of a significant number of enantiopure ligands.

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.

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.