To provide a method for producing a compound represented by the formula (1) which is a 2-pyridone compound useful as a pharmaceutical or an intermediate for a pharmaceutical, etc. at a high yield.

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A method for producing a 2-pyridone compound represented by the formula (1), which comprises reacting a 6-benzoyl-2-pyridone compound represented by the formula (3) with a sulfone compound represented by the formula (4):

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The present invention relates to the technical field of organic chemistry, specifically an asymmetrical hydrogenation of an ∂-ketonic acid compound, the technical proposal being as shown by the following formula:

##STR00001##

Wherein R.sup.1 is a phenyl, a substituted phenyl, a naphthyl a substituted naphthyl, a C.sub.1-C.sub.6 alkyl or aralkyl, the substitute is a C.sub.1-C.sub.6 alkyl, a C.sub.1-C.sub.6 alkoxy, a halogen, the number of the substituents is 1-3.

M is a chiral spiro-pyridyl amido phosphine ligand iridium complex having the following structure,

##STR00002##

Wherein, R is hydrogen, 3-methyl, 4-.sup.tBu or 6-methyl

The present invention relates to the technical field of organic chemistry, specifically an asymmetrical hydrogenation of an ∂-ketonic acid compound, the technical proposal being as shown by the following formula:

##STR00001##

Wherein R.sup.1 is a phenyl, a substituted phenyl, a naphthyl a substituted naphthyl, a C.sub.1-C.sub.6 alkyl or aralkyl, the substitute is a C.sub.1-C.sub.6 alkyl, a C.sub.1-C.sub.6 alkoxy, a halogen, the number of the substituents is 1-3.

M is a chiral spiro-pyridyl amido phosphine ligand iridium complex having the following structure,

##STR00002##

Wherein, R is hydrogen, 3-methyl, 4-.sup.tBu or 6-methyl

The present invention discloses a diphenylamine-linked chiral bis(oxazoline) ligand without C.sub.2-symmetry of formula 3 and its synthesis method and application in an asymmetric catalytic reaction, wherein C.sub.2-symmetry is lost by introducing different groups into the diphenylamine backbone to realize precise control of “electronic effect” of the ligand backbone. An anthranilic acid derivative and an orthochlorobenzoic acid derivative are used as starting materials to prepare a compound of formula 1, and then the compound of formula 1 is reacted with a chiral amino alcohol compound to prepare a β-bishydroxy amide compound of formula 2, and the compound of formula 2 is further subjected to condensation to obtain the diphenylamine-linked chiral bis(oxazoline) ligand without C.sub.2-symmetry of formula 3. The present invention also provides an application of a catalyst formed by coordination of the diphenylamine-linked chiral bis(oxazoline) ligand without C.sub.2-symmetry with copper salt, zinc salt, nickel salt, iron salt or rhodium salt, in an asymmetric catalytic reaction.

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A reactor for performing a gas/liquid biphasic high-pressure reaction with a foaming medium, comprising an interior formed by a cylindrical, vertically oriented elongate shell, a bottom and a cap, wherein the interior is divided by internals into a backmixed zone and a zone of limited backmixing, wherein the backmixed zone and the zone of limited backmixing are consecutively traversable by the reaction mixture, wherein the backmixed zone comprises means for introducing gas and liquid and a gas outlet and also comprises at least one mixing apparatus selected from a stirrer, a jet nozzle and means for injecting the gas, and the zone of limited backmixing comprises a reaction product outlet, a first cylindrical internal element which in the interior extends in the longitudinal direction of the reactor and which delimits the zone of limited backmixing from the backmixed zone, backmixing-preventing second internal elements in the form of random packings, structured packings or liquid-permeable trays arranged in the zone of limited backmixing and a riser tube whose lower end is arranged within the backmixed zone and whose upper end opens into the zone of limited backmixing so that liquid from the backmixed zone can ascend into the zone of limited backmixing via the riser tube, wherein flow into the zone of limited backmixing enters from below. The reactor is configured such that the high-pressure reaction space is optimally utilized and contamination of workup steps or subsequent reactions arranged downstream of the high-pressure reaction with foam is substantially avoided. The invention further relates to a process for performing a continuous gas/liquid biphasic high-pressure reaction in the reactor.

Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a bimetallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The catalytic complexes have exhibited the ability to achieve reaction products have a very high degree of optical purifies. These reaction products can be used as reagents in the synthesis of complex organic molecules, such as bioactive products, and C—H bond oxidation of complex molecules including various drugs and natural products.

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.

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(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.)

Chiral spirobiindane skeleton compound and preparation method thereof is disclosed in the present invention. The spirobiindane skeleton compound of the present invention having the structure formula of I or I′; the preparation method for synthesizing the spirobiindane skeleton compound of the present invention comprising the following steps: in the presence of solvent and catalysts, the structure formula compound III reacted through intramolecular Friedel-Crafts reaction to obtain the compound of formula I; the catalyst is a Browsteric acidor Lewis acid. The preparation method of chiral fused spirobiindane skeleton compound of the present invention does not need to adopt chiral starting materials or chiral resolving agents, does not require chiral resolving steps, is simple in method, is simple in post-treatment, and is economic and environment friendly. High product yield, high product optical purity and chemical purity. The catalyst for the asymmetric reaction is obtained from the chiral spirobiindane skeleton ligand of the present invention, under the catalytic reagent of transition metal, the catalyzed hydrogenation reaction can arrive at a remarkable catalytic effect with a product yield of >99%, and a product ee value of up to >99%. ##STR00001##

Chiral spirobiindane skeleton compound and preparation method thereof is disclosed in the present invention. The spirobiindane skeleton compound of the present invention having the structure formula of I or I′; the preparation method for synthesizing the spirobiindane skeleton compound of the present invention comprising the following steps: in the presence of solvent and catalysts, the structure formula compound III reacted through intramolecular Friedel-Crafts reaction to obtain the compound of formula I; the catalyst is a Browsteric acidor Lewis acid. The preparation method of chiral fused spirobiindane skeleton compound of the present invention does not need to adopt chiral starting materials or chiral resolving agents, does not require chiral resolving steps, is simple in method, is simple in post-treatment, and is economic and environment friendly. High product yield, high product optical purity and chemical purity. The catalyst for the asymmetric reaction is obtained from the chiral spirobiindane skeleton ligand of the present invention, under the catalytic reagent of transition metal, the catalyzed hydrogenation reaction can arrive at a remarkable catalytic effect with a product yield of >99%, and a product ee value of up to >99%. ##STR00001##

An object of the present invention is to provide a further more effective process for preparing a certain optically active compound including an optically active 1-acetyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline.

The present invention provides a process for an optically active compound represented by formula (3) (wherein R.sup.5 represents a hydrogen atom etc., R.sup.6 and R.sup.7 each independently represents a hydrogen atom, etc., R.sup.8 represents a C1-C6 alkyl group, and R.sup.9, R.sup.10 and R.sup.11 each independently represents a hydrogen atom, etc. The carbon atom with a symbol of the asterisked “*” represents an asymmetric carbon atom),

which comprises a reacting a compound represented by formula (2) (wherein R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, and R.sup.11 has the same meanings as the above) with hydrogen in the presence of asymmetric cobalt complex.

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