142 results about "Chiral ligand" patented technology

The application relates to a chiral NSiN ligand based on a phenyloxazoline skeleton, a preparation method and application thereof, wherein the chiral NSiN ligand is prepared from a chiral phenyloxazoline bromide with R or S configuration through lithiation and silylation. The chiral NSiN ligand can be used in transition metal catalyzed asymmetric synthesis, and is used in catalyzing an allylic sulfonylation reaction with a cobalt catalyst, and shows high reaction activity and high stereoselectivity.

This invention discloses a novel chiral bipyridine ligand, its synthesis method, and its application. The novel chiral bipyridine ligand is selected from compounds with the following structures: The chiral ligand of this invention has been successfully applied in the copper-catalyzed asymmetric ring-opening / cross-coupling reaction of cyclic diaryl iodine and secondary amine, yielding the product with excellent yield and ee value.

This invention discloses a chiral [oxyindole-pyrrolidine-β-lactam] bispirocyclic compound containing trifluoromethyl groups, with the following structural formula: The preparation includes the following steps: 1. Sequentially adding a metal catalyst, a chiral ligand, a base, indigo-derived trifluoromethylimine ylide, and 3-methylene β-lactam, followed by the addition of an organic solvent to obtain a mixture. The mixture is stirred at a reaction temperature of 0℃ to 50℃. 2. After the reaction is complete, the chiral [oxyindole-pyrrolidine-β-lactam] bispirocyclic compound containing trifluoromethyl groups is obtained through post-processing. The chiral [oxyindole-pyrrolidine-β-lactam] bispirocyclic compound containing trifluoromethyl groups prepared in this application lays a material foundation for in-depth drug activity research based on new drug development.

The invention discloses a method for preparing a chiral benzhydrol compound through asymmetric hydrogenation of o-amido benzophenone under catalysis of rhodium. The chiral rhodium catalyst is generated in situ from a metal rhodium salt and a chiral phosphine-phosphoramidite ligand in various solvents. Compared with other methods for synthesizing chiral benzhydrol, the method has the characteristics of cheap catalyst, easiness in preparation of chiral ligand, mild reaction conditions, simplicity and convenience in operation, high yield, high enantioselectivity and the like, and can be applied to large-scale preparation of chiral benzhydrol compounds. The method is also suitable for efficient preparation of the rice plant growth regulation inhibitor (S)-Inabenide, the yield can reach 92%, the enantioselectivity can reach 96%, and the method has good industrial application prospects.

The application belongs to the technical field of asymmetric catalytic synthesis, and particularly relates to an alpha-carbon chiral phosphine compound and a preparation method thereof. In a protective gas atmosphere, an asymmetric boron protonation reaction is carried out on a dienyl phosphine oxide compound shown in a structure of formula II, pinacol borate, a copper (I) catalyst, a chiral ligand, an organic alkaline compound and a proton additive in a polar organic solvent to obtain an alpha-carbon chiral phosphine compound shown in a structure of formula I; the chiral ligand is a cyclic phosphine ligand (S, S)-Ph-BPE or a cyclic phosphine ligand (R, R)-Ph-BPE. The preparation method provided by the application can synthesize the alpha-carbon chiral phosphine compound shown in the structure of formula I with high yield and excellent enantioselectivity, the synthesis method is simple and low in cost, and the alpha-carbon chiral phosphine compound can be further converted into a new optically active product.

The invention discloses a chiral indolone spirochroman compound as well as a synthesis method and application thereof, and belongs to the field of organic chemical synthesis and medicines. The structure of the compound is an indolone spirochroman skeleton with a C3-site spiro chiral center, and the synthesis method comprises the following steps: at room temperature, dissolving palladium and a chiral ligand (L) in an organic solvent, stirring, sequentially adding acetenyl cyclic carbonate (I) and a 3-substituted indolone derivative (II), stirring to react, and separating and purifying to obtain the compound. The compound provided by the invention can be efficiently converted into other indolone spirochroman compounds with novel structures through simple reaction, and has good potential application value in the research of antitumor drugs; the synthesis method disclosed by the invention is novel and has the advantages of simplicity in operation, mild reaction conditions, good substrate universality, high yield, high stereoselectivity and the like.

The application discloses a rhodium-catalyzed desymmetrization hydroformylation method for constructing polychiral center carbon ring nucleosides. The method for constructing polychiral center carbon ring nucleosides comprises the following steps: under the condition of an inert atmosphere, an acetylacetone dicarbonyl rhodium metal precursor and a chiral ligand are added into an organic solvent to prepare a catalyst solution, the catalyst solution is mixed with a substrate, and a reaction is carried out under the condition of a hydrogen atmosphere and a carbon monoxide atmosphere; after the reaction is completed, filtration and purification are carried out, and polychiral center cycloalkyl aldehyde is obtained; and the aldehyde group is converted to obtain the polychiral center carbon ring nucleosides. The method for constructing polychiral center carbon ring nucleosides has the advantages of high selectivity, wide substrate compatibility, high reaction efficiency, easy conversion of products, and the like. The whole reaction process can obtain polychiral center cycloalkyl aldehyde in one step with extremely high enantioselectivity and diastereoselectivity, the aldehyde group is converted, polychiral center carbon rings can be obtained with high yield, high dr value and high ee value, and the method is simple and easy to operate.

The application discloses a five-membered ring containing alkynyl or triazole functional group P The chiral phosphine oxide compound is obtained through Domino Heck-Sonogashira cascade reaction by taking a prochiral tertiary phosphine oxide compound containing a double ethylene group and phenylacetylene as raw materials, transition metal palladium catalyst and chiral TADDOL phosphoramidite ligand under the protection of inert gas P The chiral phosphine oxide compound has a product yield of 96% and an enantioselectivity ee value of 99%, and a diastereoselectivity dr value of greater than 20:1. The application adopts an asymmetric desymmetrization strategy, uses a Heck reaction to start and a Sonogashira reaction to end a cascade reaction, simultaneously constructs P The chiral and quaternary carbon chiral center has mild reaction conditions, simple operation and good substrate universality, provides a compound skeleton with diversity, and is successfully applied to a palladium-catalyzed asymmetric allyl substitution reaction as a chiral ligand.

The invention discloses a chiral oxazoline ligand containing an indole skeleton as well as a synthesis method and application of the chiral oxazoline ligand. The chiral ligand has a structure as shown in a formula 1, and R1 is selected from one of alkyl, substituted alkyl, aryl and substituted aryl. The chiral oxazoline ligand of the indole skeleton can realize high-enantioselectivity Friedel-Crafts reaction of an indole skeleton compound, the reaction is one of important carbon-carbon bond forming methods in organic synthesis, and a chiral indole derivative can be efficiently generated; the chiral indole derivative has important application in synthesis of natural products and bioactive compounds. In addition, raw materials used for preparing the compound are cheap and easy to obtain, the synthesis route is short, the related reaction is a basic organic chemical reaction, the process is simple and convenient, the product is easy to separate and purify, and the method is suitable for large-scale synthesis.

The application discloses chiral bis-thiophene-bis-nitrogen-oxygen ligands BbTh-2NO and BTh-2NO. The ligands comprise bis-thiophene groups and nitrogen-oxygen groups (sulfur atoms of the bis-thiophene and oxygen atoms of the nitrogen-oxygen groups belong to electron-rich coordination sites), can form six-membered ring coordination with Lewis acid soft metal palladium, thereby generating chiral ligand metal palladium complexes, and are applied as chiral ligands in asymmetric catalytic reactions. Therefore, the application has important application value in the field of asymmetric catalytic synthesis, and a synthesis method thereof is very economical and simple. The application also has good air stability, wide applicability and good compatibility for various substituents.

The invention discloses a chiral alpha-aryloxy benzoxazole acetate compound and a synthesis method thereof, and the chiral alpha-aryloxy benzoxazole acetate compound is an optically active compound with a structure as shown in the following formula I, and comprises a stereoisomer with the same chemical general formula. According to the method, a complex formed by a chiral ligand and metal is used as a catalyst, an electrochemical catalysis asymmetric aryloxylation reaction is used as a key step, and the target chiral compound is accurately and efficiently synthesized with high yield and high stereoselectivity. The preparation method is simple, reaction conditions are mild, atom economy is excellent, and the prepared chiral alpha-aryloxy benzoxazole acetate compound has good biological activity potential, can be widely applied to the field of drug intermediate synthesis and has remarkable biomedical practicability and industrial large-scale production prospects.

The application discloses a catalytic synthesis method of chiral polysubstituted hydrogenated quinoline compounds, and belongs to the field of organic synthesis. The application comprises the following steps: at 0-40 DEG C, alcohol or halogenated alkane is used as a solvent, a copper metal catalyst and a chiral ligand are added, and reaction is carried out under nitrogen protection for 0.5-2 hours; the temperature is lowered to-60-0 DEG C; then, o-aminophenyl nitrone, propargyl alcohol ester and alkali are sequentially added; and reaction is carried out for 6-48 hours, so as to obtain a chiral polysubstituted hydrogenated quinoline compound shown in formula 1 or 2. The application realizes, for the first time, synthesis of chiral polysubstituted hydrogenated quinoline compounds by using o-aminophenyl nitrone and propargyl alcohol ester as reactants, and by using a cheap copper metal catalyst and a chiral ligand, the method is simple in operation, low in cost, and has excellent enantioselectivity and diastereoselectivity.

The application discloses a method for detecting glutathione by using manganese-based chiral nanomaterials, and belongs to the field of chemical engineering, specifically to the field of analytical chemistry technology. The method comprises the following steps: taking a dispersion liquid of manganese-based chiral nanomaterials as a detection reagent, mixing the detection reagent with a sample containing glutathione to be detected, and comparing a circular dichroism spectrum signal with a standard curve to obtain the concentration of the sample containing glutathione to be detected; wherein a chiral ligand of the manganese-based chiral nanomaterials is ribose. Based on the circular dichroism spectrum detection, the detection wavelength band used is in the visible light region, is not easy to be disturbed, is sensitive, and the resolution can reach 3 muM, and the detection limit is 1.5 muM, which has important significance and value for promoting the development of the fields of optics, life science, medicine and the like.

The invention discloses a chiral P, N, N-tridentate ligand based on a ferrocene skeleton as shown in a formula I, a preparation method of an iridium catalyst containing the ligand and application of the ligand in preparation of a carbon-nitrogen axial chiral compound and a diltiazem intermediate. According to the present invention, the chiral P, N, N-tridentate ligand based on the ferrocene skeleton and the metal iridium precursor [Ir (COD) Cl] 2 are subjected to complexation to obtain the complex as the iridium catalyst, and the catalyst can be used as the iridium catalyst with characteristics of high yield (up to 99%), high enantioselectivity (up to gt; 99% ee) and high diastereoselectivity (up to gt; according to the method, N-aryl indolal or N-aryl indolone is subjected to asymmetric hydrogenation by using N-aryl indolal or N-aryl indolone (R1, R2, R3, R4, R5, R6, R7, R7, R8, R9, R9, R9, the catalyst can also be applied to asymmetric synthesis of diltiazem intermediate (2R, 3S)-3-(4-methoxyphenyl)-2, 3-epoxidized propionate, has the advantages of short synthesis route, high yield, good stereoselectivity (as high as 99% ee, 97 / 3dr) and the like, and has better economic and social benefits.

This invention provides a class of general-purpose chiral catalysts containing a cinchona primary amine arylformamide skeleton, along with their preparation methods and applications, belonging to the field of catalytic materials technology. The chiral catalysts provided by this invention link cinchona primary amine with oxazole / thiazole / imidazolium formamide structural units capable of coordination. Through the coordination of the oxazole / thiazole / imidazolium and amide coordinating groups with the central metal, they act as chiral ligands to catalyze a wider range of asymmetric reactions. They can also be used alone as chiral small-molecule catalysts for cinchona-like tertiary amine (thiourea) and square amides to catalyze asymmetric organic reactions. Furthermore, they can achieve synergistic (co-catalytic) catalysis of small molecules and metals in the same reaction system through different combinations. These chiral catalysts can be widely used as Lewis bases, Lewis acids, or small-molecule chiral catalysts and chiral ligands, possessing potential scientific and applied value in chiral sciences such as asymmetric catalysis, chiral synthesis, and chiral resolution.

The application discloses a kind of chiral dihydrofuranocoumarin compounds, its synthesis method and application, belong to organic chemistry synthesis and medical field;The structure of the compound is with C3 position amino methyl substitution chiral center dihydrofuranocoumarin as skeleton, its synthesis method is: at room temperature, copper salt and chiral ligand (L) are dissolved in organic solvent and stirred, then 4-ethynyl cyclic carbamic acid ester (I), 4-hydroxycoumarin (II) are sequentially added, after stirring reaction is completed, direct separation and purification are obtained;The compound provided by the application can be efficiently converted into other novel furanocoumarin compounds by simple reaction, and has good potential application value in antitumor drug research;The synthesis method of the application has the advantages of novelty, simple operation, mild reaction condition, good substrate universality, high yield, high stereoselectivity and the like.

The invention discloses a ferrocene nitrogen phosphine chiral ligand and a preparation method thereof, and belongs to the technical field of chemistry. The method comprises the following steps: in an inert gas atmosphere, dissolving an added 2-ferrocene vinyl quinoline compound and diphenyl phosphine oxide into a dry solvent, and then adding a chiral phosphoric acid catalyst to react to obtain the ferrocene nitrogen phosphine chiral ligand. The method has the advantages of simple and convenient steps, simple and easily available reaction conditions, rapid reaction, strong innovativeness and the like, can efficiently obtain the novel chiral ligand with excellent yield and enantioselectivity, and has good practical value and popularization prospect.

The application provides a chiral 2-position disubstituted indoline compound and a synthesis method and application thereof. The application uses a simple structure palladium catalyst and a chiral ligand as a catalyst system, and uses a newly designed allyl benzoxazinone as a raw material to perform a palladium catalyzed intramolecular asymmetric cyclization reaction, so that efficient asymmetric synthesis of the chiral 2-position disubstituted indoline compound is realized. The synthesis method is simple, the reaction condition is mild, the cost is low, and the efficiency is high; the raw material is cheap and easy to obtain, atom economy is good, and the substrate is widely applicable; the target product has high yield and high enantioselectivity; the chiral 2-position disubstituted indoline compound obtained by the application has excellent inhibition effect on bladder cancer cells, provides a scientific basis for developing a new candidate drug for treating bladder cancer, and has important significance for the treatment of bladder cancer.

The application discloses a kind of photocontrol chiral ligand based on diarylethene, structural general formula is as shown in following formula:After the photocontrol chiral ligand based on diarylethene synthesized in the application and rhodium catalyst coordination, when catalyzing asymmetric carbon hydrogen amidation at room temperature, higher reaction yield and higher ee value can be obtained by using ligand in open loop state to catalyze, and lower reaction yield and lower ee value can be obtained by using ligand in light stable state to catalyze.The application makes up the deficiency that there is currently lack of photo-thermal bistable photocontrol catalyst in the field of photocontrol asymmetric catalysis, and widens the application of diarylethene in photocontrol asymmetric catalysis.

The invention provides a method for efficiently preparing various substituted chiral phosphoramides, which comprises the following steps: in the presence of an organic solvent, alkali, a chiral ligand and a catalyst, reacting a nucleoside compound or alcohol with racemic amino phosphoryl dichloride or alkoxy phosphoryl dichloride to generate chiral phosphoryl chloride; and reacting the chiral phosphoryl chloride with a nucleophilic reagent to obtain the chiral phosphamide. The synthesis method provided by the invention is simple to operate, high in yield and good in diastereoselectivity or enantioselectivity, and the obtained target compound has the characteristics of good functional group compatibility and wide substrate universality. The obtained product is diversified in structure and good in controllability, and has good application potential in the field of medicine synthesis.

The application relates to an asymmetric catalytic synthesis method and application of chiral azido tertiary alcohol and azulenic compound. The method is characterized in that under an air atmosphere, a racemic azido tertiary alcohol compound ((+ / -) I) and tri (4-methylphenyl) phosphorus (II) are reacted in toluene by taking chiral tartaric acid derivative phosphoric acid C1, a spirochiral phosphoric acid C2 or octahydroazulene phosphoric acid C3 as a chiral catalyst, the reaction is carried out at 30 DEG C for 17-72 hours, and target chiral azido tertiary alcohol compound (I) and chiral azulenic compound (III) are obtained through separation and purification. S I) and chiral azulenic compound (III) can be used for synthesizing chiral ligand IV, and deuterium water can be added in the reaction system to be used for synthesizing chiral deuterated azulenic compound (D-III).

The application provides a method for constructing a planar chiral [2,2] paracyclophane by cobalt-catalyzed asymmetric carbon-hydrogen bond activation-kinetic resolution, which comprises the following steps: under the condition of direct current electrolysis, using a cobalt catalyst, a chiral ligand and an additive, taking a graphite felt electrode as an anode and a platinum electrode as a cathode, and allowing a racemic [2,2] paracyclophane formamide to undergo asymmetric carbon-hydrogen bond dehydrogenation coupling / kinetic resolution with an aryl acid, and after the reaction is completed, corresponding post-treatment is performed to obtain a planar chiral [2,2] paracyclophane formamide and a planar chiral oxo para-[2,2] paracyclophane. The application realizes electrochemical synthesis of the planar chiral oxo para-[2,2] paracyclophane by the method of crust-abundant transition metal catalyzed asymmetric carbon-hydrogen bond activation, the reaction substrate has wide universality, the stereoselectivity is excellent, and the product and the split-recovered raw material have excellent ee value (up to >99% ee) and a split factor (up to 1057).

The invention discloses a preparation method and application of a single-layer covalent organic framework with an adjustable chiral interface, and the method comprises the following steps: firstly, carrying out Schiff base reaction on 1, 3, 5-tri (4-aminophenyl) benzene and 2, 2 '-bipyridine-5, 5'-dialdehyde to prepare a COFTAPB-Bpy single-layer film, and transferring the COFTAPB-Bpy single-layer film to a transistor semiconductor channel; soaking in Cu (NO3) 2.3 H2O to introduce Cu < 2 + > to form a coordination center, and introducing L-alanine and other chiral ligands in a ligand exchange manner to construct an adjustable chiral interface; the single-layer structure enables chiral recognition sites to be in an effective modulation range of an electric field, weak differences between amino acid enantiomers are converted into obvious electric signal changes, and various enantiomers can be recognized under the same parent structure system by replacing chiral ligands.

The present invention relates to the field of pesticide chemistry technology, and in particular, to a method for selectively and asymmetrically hydrogenating 4-substituted-1,2-dihydroquinoline and use thereof. The present invention discloses a selective, asymmetric hydrogenation reaction conducted on 4-substituted-1,2-dihydroquinoline in the presence of a chiral ligand and a rhodium catalyst. The selective, asymmetric hydrogenation method features ease to operate, a higher conversion rate, and higher enantioselectivity.

The invention relates to a process for L-Iditol by hydrogenating L-Sorbose. Further, the invention also relates to a use of a transition metal complex as hydrogenation catalyst for L-Sorbose. The invention relates to a process for the preparation of L-Iditol comprising at least one reaction step, in which a composition comprising L-Sorbose and hydrogen is reacted in the presence of a transition metal catalyst complex in a homogeneous solution, wherein the transition metal catalyst complex comprises at least one chiral ligand containing at least one phosphorus atom, which is capable of coordinating to the transition metal, and wherein the transition metal is selected from metals of groups 8, 9 and 10 of the periodic table of the elements according to IUPAC. The invention further relates to a use of a transition metal complex as defined above and below as hydrogenation catalyst for compositions comprising L-Iditol or mixtures thereof.

This invention belongs to the field of chemical catalysis technology, and discloses a class of bridged carboxylic acid-containing bifunctionalized phosphine ligands or their racemates or enantiomers, as well as their preparation methods and applications. The bridged carboxylic acid-containing bifunctionalized phosphine ligands or their racemates or enantiomers of this invention have the structures shown in Formulas I-V: wherein, R 1 R' is a C1-C5 straight-chain alkyl group; R' is any one of substituted or unsubstituted aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. The bridged carboxylic acid-containing bifunctionalized phosphine ligand of this invention, with biphenyl as its backbone, achieves complete transfer of facet chirality to axial chirality through a desymmetry reaction via precise chiral recognition and control. The resulting chiral ligand exhibits advantages such as high reactivity, good enantioselectivity, and a wide substrate adaptability. It is particularly effective in palladium-catalyzed asymmetric C-H bond-activated arylization reactions of halogenated compounds and can be applied to asymmetric C-H bond-activated arylization reactions.

The invention discloses a method for synthesizing chiral morpholine from propargyl alcohol ester. Chiral morpholine is an important drug molecular skeleton and is widely applied to the aspects of analgesia, anesthesia, tumor resistance, heart treatment and the like as a drug active ingredient, but an efficient synthesis method is lacked. According to the method disclosed by the invention, under the regulation and control of arylboronic acid and a specific chiral ligand, propargyl alcohol ester and an affinity reagent react to obtain optically pure (87-97% ee) morpholine. The method has the characteristics that the catalyst and the ligand are wide in source, and the substrate is cheap and easy to obtain; the chiral morpholine has excellent enantioselectivity and good functional group compatibility, can be suitable for structural modification of bioactive molecules and intermediates, and is a simple and efficient asymmetric catalysis strategy for synthesizing chiral morpholine.

This invention provides a method for preparing chiral N-tert-butylsulfonamide compounds. The method uses N-tert-butylsulfonylimide as a starting material, employs Mn(CO)₅Br and a chiral PNN ligand as catalysts, and an alcohol as a solvent. A hydrogenation reaction occurs in this homogeneous catalytic system, yielding axially chiral diaryl nitrophenol compounds in high yield (99%) and with high ee values ​​(>99%). This reaction has the advantages of high efficiency, mild conditions, and environmental friendliness. The obtained chiral N-tert-butylsulfonamide can be deprotected with a sulfonyl protecting group to obtain the corresponding chiral primary amine.

This invention discloses a method for synthesizing chiral quinoxalones. Using a copper salt, a chiral ligand, and a base as a catalytic system, the target chiral quinoxalone compound is obtained by reaction in an organic solvent. This invention utilizes an economical and readily available copper catalyst, constructing C-N bonds through propargyl substitution and aminolysis of the ester group to synthesize chiral quinoxalones. This method has advantages such as good substrate universality, high yield, good enantioselectivity, and ease of industrial production. The synthesis method of this invention does not require the use of special and expensive catalysts, and the reaction conditions are simple, requiring no special reaction environment such as high-pressure hydrogen, with low requirements for reaction equipment, making it easy to scale up for industrial production.

The application discloses a synthesis method of (R)-1,3-diarylbutene compounds and belongs to the field of organic synthesis. Under visible light, a compound shown in formula 1 and a compound shown in formula 2 are used as raw materials, and under the conditions of a chiral ligand shown in formula 3, a nickel catalyst, a photocatalyst, a reducing agent and a base, a (R)-1,3-diarylbutene compound shown in formula 4 is obtained. The raw material synthesis method is simple, cheap, simple in operation steps and mild in reaction conditions.