619 results about "Chiral ligand" patented technology

The invention relates to a chiral spiro aminophosphine ligand compound and a synthesis method as well as an application thereof. The chiral spiro aminophosphine compound contains a compound with a structure shown in I, or a racemic body or an optical isomer thereof, or a catalyzed acceptable salt thereof, wherein the main structure characteristic is with a chiral spirobiindane matrix. The chiral spiro aminophosphine compound can be synthesized by taking 7-diaryl/phosphito-7'-carboxy-1, 1'-spirobiindane or substituted 7-diaryl/phosphito-7'-carboxy-1, 1'-spirobiindane as chiral starting materials, which has optical activity and spiro matrix. The chiral spiro aminophosphine compound can be used as a chiral ligand for an asymmetrically catalyzed hydrogenation of an iridium catalyzed carboxy compound and achieves high yield and enantioselectivity (97%ee). The reactive activity is also high and the consumption of the catalyst can be reduced to 0.01% molar.

A method for preparing an enantiomeric chromane, by asymmetrically hydrogenating a chromene compound in the presence of an Ir catalyst having a chiral ligand. The method includes the enantioselective preparation of enantiomeric equol. A preferred Ir catalyst has a chiral phosphineoxazoline ligand. Enantiomeric chromanes of high stereoselective purity can be obtained.

The invention relates to a bimetallic catalyst for synthetizing vertical structure regular makrolon through catalyzing and activating carbon dioxide to be copolymerized with internal compensation alkyleneoxide. The catalyst is a dual four-tooth or dual three-tooth Schiff alkali complex, of which two metal centers are connected through a biphenyl skeleton. Under the action of single or nucleophilicity co-catalyst, the catalyst can be used for catalyzing the carbon dioxide efficiently to be copolymerized with the internal compensation alkyleneoxide under mild condition and lower concentration of the catalyst to prepare the makrolon, the makrolon can be regulated when the catalyst efficiency is 104-106g polymer/mole catalyst and the polymer molecular weight is between 103 and 105, the makrolon can be regulated when the molecular weight distribution is less than 2 and the vertical structure regularity is between 60-100%, an alternate structure exceeds 98% and the makrolon can be degraded into a small molecular compound. The product selectivity and structure selectivity of the polymer compounds of the catalyst system using a chiral ligand are all above 98%, the enantiomer excess value of the mellow obtained by degradation reaches as high as 99%, so that the bimetallic catalyst provides a broad prospect for industrial application.

The invention relates to a non-interpenetrating chiral MOF (metal organic framework) stationary phase, its preparation method and application in enantiomer separation in HPLC (high-performance liquid chromatography). The stationary phase is a non-interpenetrating chiral three-dimensional porous framework complex with a structural formula as {[ZnL].H2O}n. An asymmetric structural unit {[ZnL].H2O} of the complex is composed of a Zn<2+>, an L ligand and a guest water molecule. The L ligand is -NH- containing chiral pyridine carboxylic acid, its chemical composition is [(N-(4-pyridylmethyl)-L-leucine.HBr)], and its molecular formula is C12H19BrN2O2. Chiral amino acid and 4-pyridylaldehyde are selected as raw materials to synthesize the-NH- containing pyridine carboxylic acid chiral ligand by a one-step process. The ligand and zinc acetate are adopted as raw materials to undergo room temperature diffusion so as to obtain the MOF stationary phase. The material provided in the invention has uniform chiral helical channel, uniform aperture and orifice, and can be used for separation of chiral drugs and other enantiomers. The separation is selectively dependent on the size of a separated enantiomer molecular size, but is not dependent on the functional group of the separated enantiomer. Thus, the non-interpenetrating chiral MOF stationary phase has the characteristics of traditional zeolite molecular sieve separation.

The invention discloses a preparation method and an application for phosphine-oxazoline ligand, and ionic metal complex, enantiomer or racemate thereof. The ligand and the ionic metal complex thereof have the following structural formulas. The phosphine ligand related by the invention employs biphenyl as a skeleton, and realizes completely transmission from planar chirality to axial chirality through an asymmetric desymmerization. The synthetic method is simple and economic, omits a common and complex chiral separation process in the preparation of the chiral ligand. The obtained chiral ligand has the advantages of high reactive activity, good enantiomorphous selectivity and the like in a model reaction.

A catalyst of chiral bis-oxazolinylpyridine is provided, which comprises two parts including a 4-z-2, 6-bis [4'(s)-R oxazoline-2'-] pyridine as the chiral ligand of the bis-oxazolinylpyridine, and a Scandate, Yttrium and Lanthanide metal salt. The preparation method is to mix the metal salt, the ligand of bis-oxazolinylpyridin with the equal molar quantity, and a 4-molecular sieve together, the mixture is added with the needed solvent, and then stirred under the temperature of -78 to 25 DEG C to obtain the catalyst prepared in situ. The usual dosage of the catalyst used for catalyzing Diels-Alder reaction is 1percent to 5percent of the dosage of the substrate. The catalyst can catalyze Diels-Alder reaction of both alpha, beta-unsaturated N-acetyl oxazolidone and alpha, beta-unsaturated ester with high efficiency in high selectivity. Under condition of the normal pressure with the temperature of 0 to 25 DEG C, the catalyst can accomplish the conversion rate as high as 100 percent and the enantiomeric selectivity of 96 percent.

The invention relates to the preparation method of Vortioxetine. The preparation method is characterized by comprising the steps of: obtaining a compound (formula 2) by carrying out coupling reaction on compound 2,4-dimethylbenzenethiol (formula 4) and compound 2-bromoiodobenzene (formula 3) in the presence of copper iodide, chiral ligand and alkali; obtaining a compound (formula 1) through the reaction of compound in formula 2 and piperazine in the presence of copper iodide, chiral ligand and alkali; or operating the twp steps in one reactor by one-pot method; the preparation method is easy to obtain material, simple in technology, high in product purity, few in by-products and beneficial to industrial production of the bulk drug.

The invention provides a preparation method of a mono-chiral metallic organic frame material with a function of splitting chiral amine. The method comprises the following steps of: dissolving manganese salt and mono-chiral ligand (S)-3,3'-di-tert-butyl-5,5'-di(3,5-dicarboxylphenyl)-6,6'-dimethyl-2,2'-dihydroxyl-1,1'-bipheny into methanol and N,N-dimethyl formamide according to certain proportions, stirring for 10 minutes and then heating up to 80-85 DEG C, reacting for about 24 hours to generate colorless needle-like crystals, and then washing with aether to obtain the structurally stable mono-chiral metallic organic frame material with the function of splitting the chiral amine. The preparation method provided by the invention has the characteristics that the preparation condition is mild, the operation is simple, the separation ee value of the chiral amine is higher than 90%, and the chiral amine is reusable.

The invention discloses a preparation method of an NEP (neutral endopeptidase) inhibitor intermediate, further discloses a selective reduction preparation method of the NEP inhibitor intermediate (2R, 4S)-5-([1,1'-biphenyl]-4-yl)-4-((t-butyloxycarboryl)amino)-2-methylpentanoic acid in presence of a chiral ligand, and particularly discloses a diastereoselective hydrogenation synthetic method with hydrogen under the condition of presence of a transition metal catalyst and the chiral ligand. The metal catalyst used in the method is cheap, the chiral ligand is obtained easily, high yield is realized, a high-purity product is produced preferably, and the product with the proportion of diastereoisomers being 90:10 is produced preferably.

The invention discloses a phosphine ligand and an enantiomer or a racemic body thereof and preparation methods and applications thereof. The structural formulae of the phosphine ligand and the enantiomer or the racemic body are shown in the specifications; a phosphine ligand compound has a novel framework; complete transfer of planar chirality to axial chirality in a synthesis process is realized through a desymmetrization reaction; a synthesis method is simple and economical; during preparation of a chiral ligand, common complex chiral splitting processes are avoided; and an obtained chiral ligand has the advantages of high reaction activity, high enantioselectivity and the like in a model reaction, can be applied to catalytic reactions of a plurality of metals such as palladium, rhodium, nickel, copper, iridium, ruthenium, iron, cobalt, gold, platinum and the like, and can have a very good catalytic effect.

Chiral ligands and transition metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The chiral ligands include phospholanes, P,N ligands, N,N ligands, biphenols, and chelating phosphines. The ferrocene-based irridium (R,R)-f-binaphane complex reduces imines to the corresponding amines with 95-99.6% enantioselectivity and reduces beta-substituted-alpha-arylenamides with 95% enantioselectivity. The transition metal complexes of the chiral ligands are useful in asymmetric reactions such as asymmetric hydrogenation of imines, asymmetric hydride transfer reactions, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, allylic alkylation, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition and epoxidation reactions.

The invention relates to a synthesis method for stereoregularity polyester and a bi-metallic catalyst. The catalyst is a bi-nuclear metal complex formed by connecting two metal centers through a biphenyl or dinaphthalene framework. The catalyst can efficiently catalyze a cyclic anhydride and internal compensation epoxyalkane polymerization reaction under the mild condition and low catalyst concentration to prepare polyester under the effect of a nucleophilic co-catalyst, the catalysis efficiency is 103-106 g of a polymer per mole of the catalyst, the molecular weight of the polymer can be adjusted within the range of 103-105, the molecular weight distribution is smaller than 2, stereoregularity can be adjusted within the range of 60-100%, the alternative structure exceeds 98%, and polyester can be degraded into a small molecular compound under a certain condition. A chiral ligand catalytic system is used, the product selectivity and alternative structure selectivity of the polymer are both higher than 98%, the excess value of enantiomer of diol obtained after degradation is higher than 70%, and wide prospects are provided for industrial application.

A spirocyclosulphite is prepared from spirocyclodiphenol through three methods. Its spirodihydroindene structure has axial chirality, so said compound has two mutamers: levo- and dextro- spirocyclosulphite compounds. It can be used for the asymmetrical addition reaction of aldehyde and imine with high stereo activity.

The invention relates to chirality phosphine ligand metal complex catalyse system, which is composed by complex formed by ligand and metal Rh, Ru, Ir, Pt or Pd or ligand and metal precursor in of 1-2 mol ratio. The phosphine ligand is a kind of effective chirality phosphate ligand composed by D-mannitol or L-mannitol after reaction. The catalyst composed by the chirality ligand and rhodium metallic compound in asymmetry hydrogenation reaction can work in room temperature. With a wide applied range, catalyst's activation and stereoselectivity is not influenced from normal pressure to high pressure. Reaction time is 1-24 hours. Mol ratio of ligand and metal rhodium compound is 1:1-2:1. Ratio of reactant and catalyst is 100-10,000.

The present invention provides an osmium oxide composition comprising an osmium oxide microencapsulated in an aromatic polyolefin (hereinafter abbreviated as MCOsOx), a method for preparation of MCOsOx, which comprises allowing an osmium oxide to contact with an aromatic polyolefin in an organic solvent, and precipitating MCOsOx, an oxidizing agent comprising MCOsOx, a method for preparing a chiral diol compound, which comprises reacting MCOsOx, a chiral ligand and an olefin compound with each other, and a method for preparing a chiral diol compound, which comprises oxidizing an olefin compound with MCOsOx wherein a chiral ligand further coordinates to an osmium oxide.

Chiral ligands and transition metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The chiral ligands include (R,S,S,R)-DIOP*. The ruthenium complex reduces enamide to the corresponding amine with up to 99% enantioselectivity. The transition metal complexes of the chiral ligands are useful in asymmetric reactions such as asymmetric hydrogenation, hydride transfer, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, hydrocarboxylation, isomerization, allylic alkylation, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition and epoxidation reactions.

The invention provides a method for synthesizing derivatives of chiral tetrahydroquinoline by catalyzing asymmetric hydrosilylation with iridium. In the method, a used catalytic system is a chiral duplex phosphorus complex generated in situ. The reaction can be performed under the following conditions: a room temperature; a tetrahydrofuran solvent; a chlorizated cyclooctadiene iridium metallic precursor; and a chiral duplex phosphorus ligand chiral ligand. The method for preparing the catalyst comprises the following steps of: stirring the metallic precursor of iridium and the chiral duplex phosphorus ligand in the tetrahydrofuran at room temperature, adding the simple substance of iodine, stirring the mixture, and finally adding quinoline substrates, triethyl silicon hydrogen and water. By the hydrosilylation of quinoline, the corresponding derivatives of chiral tetrahydroquinoline are obtained, and the enantiomeric excess of the derivatives reaches 93 percent. The method has the advantages of easy and practical operation, readily available raw materials, high antipodal selectivity, high yield, no use of dangerous articles such as hydrogen gas and the like, safety and reliability; in addition, the reaction is environment-friendly.

The invention discloses a preparation method of high-optical purity bortezomib and an intermediate of bortezomib, and belongs to the field of pharmaceutical synthesis. The invention discloses a synthetic method of bortezomib or boric anhydride thereof and related intermediate of bortezomib or boric anhydride. The invention firstly discloses bortezomib intermediate shown in a formula A and a preparation method thereof, and further discloses a method for preparing bortezomib by the intermediate. The bortezomib, which is obtained by introducing novel chiral ligand in the method, is high optical purity, low in material cost, easily available, simple and convenient to operate in the process, capable of greatly lowering the production cost of the process, high in product yield, high in optical purity and suitable for the industrial production of bortezomib, wherein R is Cl, Br, NH2 or FORMULA; and R1 is hydrogen or an amino protecting group.

The invention discloses a chiral MOF (Metal-Organic Framework) composite material catalyst as well as a preparation method and application thereof to detection of a chiral enantiomer based on the composite material, and belongs to the technical fields of nano composite materials, MOF materials and chiral sensory detection. The preparation method comprises the following main steps of blending an alkaline aqueous solution of a chiral ligand with an aqueous solution of copper acetate-graphene oxide-surfactant, standing at a room temperature, centrifugally separating, washing with water, and drying, so that the chiral MOF composite material catalyst is prepared. A chiral sensor constructed by adopting the composite material is used for detecting the contents of D-(+)-tryptophan and L-(-)-tryptophan enantiomers, and the method is simple, and is easy to operate and obvious in chiral detection effect.