41 results about "Asymmetric induction" patented technology

A method of determining an overlay error. Measuring an overlay target having process-induced asymmetry. Constructing a model of the target. Modifying the model, e.g., by moving one of the structures to compensate for the asymmetry. Calculating an asymmetry-induced overlay error using the modified model. Determining an overlay error in a production target by subtracting the asymmetry-induced overlay error from a measured overlay error. In one example, the model is modified by varying asymmetry p(n′), p(n″) and the calculating an asymmetry-induced overlay error is repeated for a plurality of scatterometer measurement recipes and the step of determining an overlay error in a production target uses the calculated asymmetry-induced overlay errors to select an optimum scatterometer measurement recipe used to measure the production target.

The present invention discloses non-enantioselective preparation process of emtricitabine. The preparation process includes condensation of glyoxalic acid as the initial material and 2, 5-dihydroxy-1, 4-dithiane under the asymmetric induction of optically active alcohol ester to obtain trans-5-hydroxy-1, 3-oxythiacyclopentane-2-carboxylate; halogenating and coupling with silylated 5-flucytosine, and reducing to obtain initial product; reaction with salicylic acid to form salt, purification and separation to obtain optically pure emtricitabine. The present invention has mild reaction condition, simple operation, low cost, less environmental pollution and high product purity reaching medicinal standard, and is suitable for industrial production. The product is used in treating hepatitis B and AIDS.

The present invention relates to a production method of an optically active form of a compound represented by formula (II) wherein ring A is a benzene ring optionally having substituent(s); R1 is H, a hydrocarbon group optionally having substituent(s), an acyl group or an acyloxy group; R2, R3 and R4 are each H, an alkyl group optionally having substituent(s), an alkoxy group optionally having substituent(s) or an amino group optionally having substituent(s); X is N or CH; Y is N or CH; and * shows an asymmetric center, or a salt thereof, which includes reacting a compound represented by the formula (I) wherein each symbol is as defined above, or a salt thereof, with an excess amount of an oxidizing agent in the presence of a catalyst for asymmetric induction, and provides an efficient production method of an optically active sulfoxide derivative in high yield on an industrial large scale by a convenient method, while achieving an extremely high enantiomer excess.

The iridium catalyzed enantiotropic hydrosubstituting process of aromatic pyridine ring and pyrazine ring uses catalyst system comprising chiral coordination compound of iridium and additive compound. The reaction conditions includes temperature of 0-80 deg.c; solvent of dichloromethane, toluene, tetrahydrofuaran, 1, 2-dichloro ethane, isopropanol, etc.; additive compound of tetrabutyl ammonium iodide, iodine, amine, etc.; pressure of 1-100 atm; substrate / catalyst ratio up to 5000; and chiral coordination compound of diphosphine, N-P compound, S-P compound, etc. The catalyst system is prepared through reaction of iridium precursor and chiral compound in the said solvent and the addition of the additive compound while stirring; and can produce asymmetrical induction up to 96 %. The process of the present invention is environment friendly.

Provided is a nanostructured polyphase biomimetic catalyst of quinine and a process for preparing same, belonging to the catalytic field of preparing technology of biomimetic catalyst. The method for preparation of the novel catalyst is that mesoporous material with a nanometer-sized bore diameter is employed to be a vector, a functional group provided by the vector is employed to be a first platform and reacts with substance which has active primitives, and further a second reactive platform is provided and is assembled in situ inside a nanostructured space, thereby forming the objective catalyst. The catalyst has the characteristics that active components are assembled via high dispersion in a one-dimensional or three-dimensional straight-through nanometer-sized pore passage, forming a nanostructured chiral molecule reactor, and displaying the high asymmetric inductivity. The value of the catalyst is higher than the homogeneous phase catalytic level, and the catalyst has the high reutilization property and important adaptation value. Further, the invention is easy to be commercially developed.

A process for producing an optically active isomer of a compound represented by the formula (II) (wherein ring A represents an optionally substituted benzene ring; R<1> represents hydrogen, an optionally substituted hydrocarbon group, acyl, or acyloxy; R<2>, R<3>, and R<4> each represents hydrogen, optionally substituted alkyl, optionally substituted alkoxy, or optionally substituted amino; X represents nitrogen or CH; Y represents nitrogen or CH; and * indicates an asymmetric center) or of a salt of the compound, characterized by reacting a compound represented by the formula (I) (wherein the symbols have the same meanings as the above) or a salt thereof with an excess of an oxidizing agent in the presence of a catalyst for asymmetry induction. This process is a simple process by which an optically active sulfoxide derivative can be efficiently and industrially mass-produced in high yield while attaining an extremely high enantiomer excess.

The invention relates to a method for preparing chiral beta-amino arylbutyric acid derivatives (as shown in a structural formula I). The method comprises the following steps: condensing aryl acetoacetic ester with chiral alkamine; carrying out asymmetric induction reduction so as to obtain annular chiral beta-amino arylbutyric acid derivatives (as shown in a structural formula II); and hydrogenating the compound II so as to prepare chiral beta-amino arylbutyric acid derivatives (as shown in the structural formula I). The method is convenient for operation, low in cost and suitable for large-scale production, and the optical purity of the obtained product is high (more than 99.0% ee (enantiomeric excess)).

The invention relates to the field of chemical catalysis and discloses a phosphoramidite ligand as well as a preparation method and an application thereof. The synthesized phosphoramidite ligand and an enantiomer or a racemate of the phosphoramidite ligand take biphenyl as a framework and are subjected to an asymmetric induced reaction of axial chirality to realize complete transfer from central chirality to axial chirality. A synthetic method for the phosphoramidite ligand and the enantiomer or the racemate of the phosphoramidite ligand is simple and economic, and a common and complex chiral resolution process is avoided during chiral ligand preparation. The phosphoramidite ligand and the enantiomer or the racemate of the phosphoramidite ligand is employed to form the ligand together with active metal-iridium for catalyzing an asymmetric addition reaction of N-protected isatin and arylboronic acid, a very good catalytic effect is achieved, and a product can obtain the yield of more than 96% and the enantiomeric excess (ee) value of more than 92%.

A method of determining an overlay error. Measuring an overlay target having process-induced asymmetry. Constructing a model of the target. Modifying the model, e.g., by moving one of the structures to compensate for the asymmetry. Calculating an asymmetry-induced overlay error using the modified model. Determining an overlay error in a production target by subtracting the asymmetry-induced overlay error from a measured overlay error. In one example, the model is modified by varying asymmetry p(n′), p(n″) and the calculating an asymmetry-induced overlay error is repeated for a plurality of scatterometer measurement recipes and the step of determining an overlay error in a production target uses the calculated asymmetry-induced overlay errors to select an optimum scatterometer measurement recipe used to measure the production target.

The invention relates to a preparation method for efficient synthesis of (R)-lansoprazole, and according to the method, in the presence of an asymmetric induction catalyst, an oxidant with 1.3 to 1.5 times molar equivalent relative to prochiral compound lansoprazole thioether is used for selective catalytic oxidation to obtain the (R)-lansoprazole. The method has the advantages of being economic, environmentally friendly, high efficiency, high in optical purity and high in chemical purity of products, and is a method suitable for industrialized production.

The invention relates to cinchona alkaloid quaternary ammonium salt derivatives and a synthesis method thereof as well as application of the derivatives in synthetizing high optical purity natural amino acid and non-natural amino acid. A structural general formula (I) represents a chiral cinchona alkaloid quaternary ammonium salt, wherein R1 is methoxyl, hydroxyl, hydrosulfuryl or hydrogen; R2 is alkyl with 3 to 20 carbon atoms; X is halogen; and n is a positive integer from 1 to 4. The cinchona alkaloid quaternary ammonium salt catalyst has high activity in an alkylation reaction, good stereoselectivity, high catalysis efficiency, a wide substrate range and good asymmetric induction.

The invention discloses an asymmetric induction catalytic synthesis method for L-muscone. The L-muscone is prepared by performing asymmetric induction catalytic synthesis on N-3-methyl-cyclopentadecane alkenyl benzylamine which is obtained by asymmetrically converting a racemate compound for multiple times and used as raw materials in the presence of an organo-transition metal complex inducing catalyst. The method has the prominent advantages of high economic benefit, simple synthesis process and low synthesis temperature.

The present invention relates to a kind of planar chiral [2,2]-p-cyclo-aralkyl oxazolinyl phosphine ligand and its synthesis and use. The compound is prepared through the reaction between chiral [2,2]-p-cyclo- oxazolinyl bromide and dibasic phosphine chloride R2'PCl in the presence of alkali. The ligand has two chiral factors of planar chirality and central chirality as well as convertibility of phosphine substituent and oxazolinyl ring substituent, and thus strong adaptability to different asymmetrical catalytic reaction. For example, it has good asymmetrical induction result in Pd catalyzed asymmetrical alloy substituting reaction and copper catalytic asymmetrical 1,4-addition reaction. The ligand has high chemical stability, simple synthesis and is suitable for use in industrial production.

The invention relates to a ferrocene ligand having central chirality and planar chirality, method for synthesizing and use thereof. The ligand has the central chirality of diamines, and is obtained through condensation of ferrocene phosphine aldehyde and chiral diamine, and further reduction, the ligand can be purified through recrystallization and column chromatography. The ligand can be used as catalyst in asymmetric alkylation reaction.

The invention discloses a synthesis method of cinacalcet hydrochloride and an intermediate thereof. The cinacalcet hydrochloride is prepared by carrying out asymmetric reduction ammonification on 3-(3-(trifluoromethyl)phenyl)propyl-1-amine and 1-(naphthyl-1-yl)ethyl ketone. The asymmetric reduction ammonification is performed by carrying out asymmetric induction by combining a Hantzsch ester and a chiral phosphine ligand. The 3-(3-(trifluoromethyl)phenyl)propyl-1-amine is prepared by the following steps: carrying out Heck coupling reaction on 3-bromo-1-trifluoromethyl benzene and acrylonitrile to obtain 3-(3-(trifluoromethyl)phenyl)acrylonitrile, and carrying out catalytic hydrogenation. The catalyst of the Heck coupling reaction is tetra(triphenylphosphine) palladium, DBA palladium or palladium acetate. The method for synthesizing cinacalcet hydrochloride greatly lowers the production cost, and is suitable for industrialized mass production. The method for synthesizing the 3-(3-(trifluoromethyl)phenyl)propyl-1-amine greatly lowers the production cost, and has higher yield.

The method of catalyzing hydrogenation of ketone enantioselectively with homogeneous Pt catalyst system has chiral diphosphorus complex of Pt as catalyst system, reaction temperature of 25-75deg.c, solvent of 2, 2, 2-trifluoroethanol, reaction pressure of 3-70 atm and chiral diphosphorus ligand used. The homogeneous Pt catalyst system is prepared through mixing metal precursor of Pt and chiral diphosphorus ligand at room temperature and the subsequent vacuum concentrating. The catalyst can result in asymmetrical inducing as high as 92 % on alpha-one-benzamide substituted ketone. The present invention has simple operation, facile material, high reaction selectivity, high yield and environment friendship.

A metal complex as catalyst with wide range of application is prepared from chiral spirocyclic mono-phosphorus (mono-phosphine) ligand and Ni. It can be used in asymmetrical olefinic hydrogenation reaction to obtain a compound with chiral center. Its preparing process is also disclosed.

The invention provides (RP)-menthyl phenyl oxygen phosphine and a synthesis method thereof. The synthesis method comprises the following steps of (1) preparing a menthyl magnesium halide or a menthyl lithium solution; (2) enabling the menthyl magnesium halide or the menthyl lithium solution to react with phenyl phosphine dichloride; (3) hydrolyzing the phenyl menthyl phosphine chloride; (4) performing post-treatment. According to the method, the obtained phenyl menthyl oxygen phosphine has a better asymmetric induction effect as containing a large-volume of mint group; besides, the chiral menthyl facilitates the stabilization of phosphorus atom configuration.

The invention discloses a biphenyl ligand, a synthetic method thereof and an application thereof in an asymmetric methoxyl carbonylation reaction, catalyzed by palladium, of racemized propargyl alcohol carbonate, wherein the biphenyl ligand is R-(+)-2,2'-bis(di(3,5,dimethoxyphenyl)-6,6'-dimethoxy-1,1'-biphenyl. The biphenyl can achieve asymmetric induction to the methoxyl carbonylation reaction of the racemized propargyl alcohol carbonate and 2,3-allenoate having higher optical purity can be prepared in high efficiency.

The invention relates to an asymmetric oxidation method for dexlansoprazole. The invention provides a method for producing 2-[[3-methyl-4-(2,2,2-trifluoroethoxyl)pyridine-2-radical]methylsulfinyl]-1H-benzimidazole. The method comprises the step of: in an organic solvent, performing the oxidation reaction on 2-[3-methyl-4-(2,2,2-trifluoroethoxyl)-2-pyridine]methylsulfonyl-1H-benzimidazole and an oxidizing agent under the existence of an asymmetric induction effect catalyst and alkali. The method is characterized in that the quantity of the oxidizing agent is about 1.2-1.4 molar equivalents relative to the 2-[3-methyl-4-(2,2,2-trifluoroethoxyl)-2-pyridine]methylsulfonyl-1H-benzimidazole. According to the production method disclosed by the invention, by controlling the use quantity of the oxidizing agent, raw materials can be completely converted and over oxidation is also avoided, so that target optical rotation sulfoxide derivatives can be effectively and industrially prepared under high yield and in a large scale by the convenient method, meanwhile, quite high enantioselectivty is realized and the quantity of over oxidation byproducts is very small.

The invention relates to an asymmetric hydrogenation method for ketone compounds, comprising the step of: under hydrogen atmosphere, in the presence of an in situ catalyst derived from a chiral ligand and a ruthenium salt, adding a ketone compound and a base into a second solvent to carry out an asymmetric hydrogenation for the ketone compound. The invention can obtain a conversion of 100% and a highest asymmetric inducement effect of 99.7% for the ketone compound. The invention has the advantages including simple procedure, high conversion and selectivity, good atom economy and good prospect of industrial application.

The invention discloses a preparation method of (R)-2-[[[3[methyl-4-nitro-2-pyridyl]methyl]sulfinyl]benzimidazole. The preparation method is characterized in that the preparation method comprises a step that 2-[[[3[methyl-4-nitro-2-pyridyl]methyl]thio]benzimidazole or its salt reacts with an excess oxidant in a solvent in the presence of an asymmetric induction effect catalyst, and the molar ratio of the 2-[[[3[methyl-4-nitro-2-pyridyl]methyl]thio]benzimidazole or its salt to the oxidant is 1:1-1:2.0. The optical purity and the yield of (R)-2-[[[3[methyl-4-nitro-2-pyridyl]methyl]sulfinyl]benzimidazole prepared through the method of the invention are extremely high.

Provided are a novel 1,2-bis(dialkylphosphino)-4,5-(methylenedioxy)benzene derivative that forms a metal complex having particularly high asymmetry induction capacity and catalytic activity on β-dehydroamino acids, a method for manufacturing the same, a metal complex having this 1,2-bis(dialkylphosphino)-4,5-(methylenedioxy)benzene derivative as a ligand, and an asymmetric hydrogenation method using this metal complex. A 1,2-bis(dialkylphosphino)-4,5-(methylenedioxy)benzene derivative represented by general formula (1). (In the formula, R1 and R2 represent an alkyl group having 1-10 carbon atoms, and R1 and R2 have different numbers of carbon atoms.)

The invention discloses a planar chiral double-reactive center ruthenium catalyst, synthesis and an application thereof. The planar chiral double-reactive center ruthenium catalyst provided by the invention not only is simple in synthesis, but also has double reactive centers, and can be used efficiently for asymmetric catalytic hydrogenation of beta-aminoketone compounds; and finally a conversion rate of 100% and an asymmetric induction effect of more than 99.9% can be achieved. The synthesis of the catalyst of the invention is simple in operation, and high in selectivity and yield, and has good atom economy and good industrial application prospects.

The invention discloses a graphene adsorption multi-component chiral catalyst and application thereof in asymmetric hydrogenation, and belongs to the field of organic chemistry. A hybrid material multi-component chiral catalyst 2a @ graphene adsorbed on graphene is prepared by using an in-situ immobilization strategy, and when the catalyst is applied to hydrogenation of a dehydroamino acid derivative, a good asymmetric induction effect is shown, and the conversion rate reaches 99% or above and the highest ee is 96%. And after the reaction is finished, recycling can be realized through simple filtration. The graphene adsorption multi-component chiral catalyst provides a good reference for developing other heterogeneous hybrid chiral catalysts based on non-covalent interaction asymmetric reaction.

An object of the present application is to provide a novel ruthenium complex which does not require addition of a base to activate it as a catalyst, has excellent crystallinity and stability, is easy to synthesize in large scale and store for a long period of time, and has excellent catalytic activity and asymmetric induction ability in an asymmetric hydrogenation reaction. The present application relates to a ruthenium complex represented by general formula (1). [The definitions of the groups in formula (1) are as described in the specification.]

The invention particularly relates to a sandwich-type luminescent material with a chiral binaphthalene skeleton, a preparation method and application. The invention discloses a luminescent material which is efficiently constructed based on multiple nucleophilic arylation reaction of chiral binaphthalene and o-benzene double nucleophilic reagents and tetrafluoro-p-diphenyl nitrile and has sandwich-type structural characteristics, and the luminescent material is characterized in that enhanced asymmetric induction and space charge transfer effects are realized through sandwich structural design. The material has solution-state efficient luminescence performance and aggregation-induced emission (AIE) characteristics, and shows excellent fluorescence quantum yield and circularly polarized luminescence performance. The compound has the advantages of being low in raw material cost, simple and reliable in preparation process, rich and adjustable in structure and the like, the luminescence color and performance of the compound can be accurately designed through a molecular structure, and the compound is suitable for the fields of photoelectric functional materials, information encryption, anti-counterfeiting marks and the like and shows good industrial application potential.

The invention relates to the field of chemical catalysis, and discloses a kind of phosphoramidite ligand, its preparation method and application. The synthesized phosphoramidite ligands and their enantiomers or their racemates use biphenyl as the backbone, and undergo a central chiral asymmetric induction reaction to achieve complete central chirality to axial chirality transfer. The synthesis method of the phosphoramidite ligand and its enantiomer or its raceme is simple and economical, and the common and complicated chiral resolution process is avoided when preparing the chiral ligand. The present invention uses phosphoramidite ligands and their enantiomers or their racemates to form complexes with active metal iridium to catalyze the asymmetric addition reaction of N-protected isatin and arylboronic acid, and obtains a good catalytic effect. The product can be obtained in a yield of more than 96% and an enantiomeric excess (ee) value of more than 92%.

The invention discloses a chiral double reaction center ruthenium catalyst as well as its synthesis and application. The chiral double-reaction center ruthenium catalyst provided by the present invention is not only easy to synthesize, but also the double-reaction center ruthenium catalyst it has can be efficiently applied to the asymmetric catalytic hydrogenation of β-aminoketone compounds; finally, 100% conversion can be obtained rate and more than 99.9% asymmetry induction effect. The synthesis operation of the catalyst described in the invention is simple and convenient, the selectivity and yield are high, the catalyst has good atom economy and good industrial application prospect.

Provided is a nanostructured polyphase biomimetic catalyst of quinine and a process for preparing same, belonging to the catalytic field of preparing technology of biomimetic catalyst. The method for preparation of the novel catalyst is that mesoporous material with a nanometer-sized bore diameter is employed to be a vector, a functional group provided by the vector is employed to be a first platform and reacts with substance which has active primitives, and further a second reactive platform is provided and is assembled in situ inside a nanostructured space, thereby forming the objective catalyst. The catalyst has the characteristics that active components are assembled via high dispersion in a one-dimensional or three-dimensional straight-through nanometer-sized pore passage, forming a nanostructured chiral molecule reactor, and displaying the high asymmetric inductivity. The value of the catalyst is higher than the homogeneous phase catalytic level, and the catalyst has the high reutilization property and important adaptation value. Further, the invention is easy to be commercially developed.