498results about "Asymmetric syntheses" patented technology

The invention provides a novel chiral ferrocene bridged binaphthyl skeleton phosphine ligand and application thereof. The ligand has the advantages of low cost, simplicity in synthesis, air stability and the like. The ligands have good catalytic activity and enantioselectivity in the asymmetric hydrogenation reaction of ketone, and have certain industrial application prospects in the synthesis of pharmaceutical molecules.

The invention relates to a method for preparing S-citalopram based on an R-diol intermediate. The method comprises the following steps: (1) carrying out SN2 configuration inversion on a citalopram R-diol intermediate under the action of a large-steric-hindrance acid and a large-steric-hindrance ligand to obtain a mixture containing S-citalopram and R-citalopram; and (2) obtaining the S-citalopram from the mixture in the step (1) under the action of a resolving agent. In addition, the invention also discloses a preparation method of the S-citalopram. The optical purity of the S-citalopram prepared by the method is greater than 95%, and the optical purity is greater than 99% after the S-citalopram is purified. In addition, the total yield of S-citalopram is increased to 82% from 31% in the prior art.

The invention provides a two-dimensional cyclodextrin polymer material as well as a preparation method and application thereof. The two-dimensional cyclodextrin polymer material is prepared by a method comprising the following steps: stirring a self-assembly agent and cyclodextrin molecules in a solvent, standing, and carrying out self-assembly to form a dispersion liquid with a sheet structure crystal; and mixing the dispersion liquid with a cross-linking agent, reacting, carrying out solid-liquid separation, washing and drying to obtain the product. The method is simple and convenient in preparation process, the two-dimensional cyclodextrin polymer with monomolecular layer thickness is obtained, and the method has considerable industrial application prospects. The invention also provides a two-dimensional cyclodextrin polymer material and application thereof.

The invention belongs to the technical field of organic electroluminescent materials, and particularly discloses a paracyclophane-based purple light chiral host material and application thereof. Paracyclophane is used as a molecular structure center, two paracyclophane derivatives are constructed, and the novel purple light chiral main body material is synthesized by combining indole carbazole groups on the periphery. Because the periphery is combined with an indolocarbazole group, the excellent photophysical property of indolocarbazole can be fully utilized, and through separation of cycloarane, intermolecular conjugation is broken, a novel purple light material is constructed, emission of 372 nm is realized, relatively high S1 and T1 energy levels are obtained, a chiral signal is provided for participation of cycloarane, and the material has a wide application prospect. The important significance is provided for constructing a novel chiral main body material.

To provide a novel stereoselective method for producing a cyclic dinucleotide derivative that can be used for an antibody-immunostimulator conjugate, and a production intermediate thereof, and to provide methods for producing a cyclic dinucleotide-linker and antibody-immunostimulator conjugate using the production method.SOLUTION: The present invention relates to a method that makes it possible to produce, in large amounts and with high yield, a cyclic dinucleotide derivative having a desired steric configuration, by using an optically active phosphitylation agent twice, during coupling and cyclization.SELECTED DRAWING: None

The invention discloses a chiral ferrocene framework tetradentate ligand and application thereof in asymmetric hydrogenation reaction. The ligand has the advantages of low cost, simplicity and convenience in synthesis, good stability and the like. A metal complex of the ligand shows very excellent catalytic activity and extremely high enantioselectivity in an asymmetric hydrogenation reaction of ketone, can efficiently catalyze reduction of prochiral ketones such as aryl alkyl ketone, heteroaryl alkyl ketone, aryl (hetero) aryl ketone and the like into corresponding chiral alcohol, and has huge industrial application potential.

The invention disclosed herein relates to metal-catalyst free, green enantioselective synthesis of sulfoxide compounds of Formula-I. Particularly, the present invention relates to in situ process to obtain enantioselective sulfoxide compounds of Formula-I with high yield and purity and specific optical rotation. Further, the enantioselective sulfoxide compounds of Formula-I are useful in the treatment of neurological, neuropsychiatric, metabolic and neurodevelopmental disorder.

The present application provides a synthetic process for production of lipoxin B4 and analogues thereof, which is modular and scalable, thus permitting synthesis of large quantities of LXB4 and analogues thereof, including radiolabeled analogues. Also provided are intermediate compounds that are useful in the synthetic process for production of lipoxin B4 and analogues thereof.

The purpose of the present invention is to provide a method for more efficiently producing specific optically active compounds including optically active 1-acetyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline.　The present invention provides a method for producing an optically active compound represented by formula (3) (wherein R5 represents a hydrogen atom, etc., R6 and R7 each independently represent a hydrogen atom, etc., R8 represents a C1-C6 alkyl group, R9, R10, and R11 each independently represent a hydrogen atom, etc., and the asterisked carbon atom is an asymmetric carbon atom), the method comprising reacting a compound represented by formula (2) (wherein R5, R6, R7, R8, R9, R10, and R11 respectively have the same meanings as defined above) with hydrogen in the presence of an asymmetric cobalt complex.

Disclosed herein is a method for preparing tertiary alcohols from optionally substituted phenyl ketones or optionally substituted pyridinyl ketones, comprising the use of chiral ligands and boron trifluoride diethyl etherate. The tertiary alcohols can be used to prepare synthetic versions of natural products and / or pharmaceuticals.

The invention provides a 1-phosphorus-doped norbornene-dimethyl xanthene chiral ligand as well as a synthesis method and application of the 1-phosphorus-doped norbornene-dimethyl xanthene chiral ligand. The structural formula of the chiral ligand is shown as a formula III and a formula III ': # imgabs0 #, a group R is C1-6 alkyl, C1-6 alkoxy, C1-6 alkenyl, phenyl, halogenated phenyl, C1-6 alkyl substituted phenyl or C1-6 alkoxy substituted phenyl, and a group R1 is C1-6 alkyl. The chiral ligand serves as a chiral phosphine ligand with a novel structure, three completely bound P-C bonds are formed through introduction of a rigid framework, the scientific problem that a phosphorus chiral center is easy to racemize is successfully solved, the phosphorus chiral ligand can be widely applied to asymmetric reactions such as asymmetric cyclization catalyzed by metal, and the phosphorus chiral ligand has a wide application prospect. And the method has a wide commercial application prospect. The synthesis method of the chiral ligand comprises the steps that the 9, 9-dimethyl xanthene compound and the 1-phosphorus-doped norbornene amine compound serve as raw materials, the chiral ligand is generated through H [1, 5] migration and phosphorus-doped D-A reaction, and the synthesis method is simple, good in feasibility and high in yield.

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 chiral 1, 4-diazabicyclo [3.1. 1] heptane derivative as well as a synthesis method and application of the chiral 1, 4-diazabicyclo [3.1. 1] heptane derivative. According to the invention, a 1-azabicyclo [1.1. 0] butane derivative is taken as a raw material, under the catalytic action of a chiral iridium complex, the 1-azabicyclo [1.1. 1] butane derivative and an N-allyl carbonate derivative are subjected to [3 + 2] cycloaddition reaction, a series of chiral 1, 4-diazabicyclo [3.1. 1] heptane skeletons with diversified structures are constructed with high stereoselectivity, and the obtained product has the potential of further derivatization. The method has the advantages of easily available raw materials, mild reaction conditions, simplicity and convenience in operation, good functional group compatibility and the like.

The invention provides an efficient method for asymmetric hydroarylation of internal olefin. The method provided by the invention has the advantages of high yield, simple operation, mild reaction conditions, strong chiral control ability and wide substrate applicability, and has high academic and application values.

The present invention relates to the preparation of amino acid derivatives VII, including the use of catalysts. The structure of the catalyst disclosed by the invention can be shown as a formula (VI), or the catalyst is loaded on a molecular sieve, and the structure of the catalyst is shown as a formula (I). The invention also discloses preparation of the catalyst and intermediates thereof. A plurality of molecules prepared by the method are all of brand new structures, and are of great significance.

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 invention discloses a benzoxphosphine ligand and a complex and application thereof. The structure of the benzoxphosphine ligand is shown as a formula (I), in the formula (I), R1 is alkyl or aryl substituted oxazolidinyl or imidazoline, R2 is alkyl and / or aryl, and R3 is at least one of fluorine, carbazolyl and 2, 6-dimethoxyphenyl. According to the benzoxphosphine ligand disclosed by the invention, the metal iridium complex can be used as a catalyst to be applied to an asymmetric hydrogenation reaction of alpha-phenyl vinyl diethyl phosphate, and has excellent activity and relatively high enantioselectivity; moreover, the benzoxphosphine ligand disclosed by the invention can be directly synthesized from simple and easily available chiral aldehyde, and the preparation method is simple and easy to operate.

The application belongs to the technical field of chemical synthesis, and specifically provides a chiral hydroxyphosphonate, a preparation method and application thereof. The chiral hydroxyphosphonate has a structure as shown in formula II: each R is independently H, an alkyl group, an alkenyl group, an alkynyl group or a halogenated alkyl group; Ar is an aromatic ring or a heteroaromatic ring; X is a bond, -O-, -N(R 1 )- 2 q , -S(=O) m -; the chiral hydroxyphosphonate is obtained by reducing an alpha phosphonate substituted benzocycloalkanone compound through an asymmetric hydrogenation method, has two chiral centers, and has a yield of up to 99% and an enantiomeric selectivity of up to 99%. The chiral hydroxyphosphonate has wide application potential and value in skin tissue soothing, repairing, anti-aging and the like.​

The invention discloses a preparation method of an optically pure mepivacaine hydrochloride intermediate. According to the method, N-(2, 6-dimethylphenyl) pyridine carboxamide is used as a starting material, hydrogenation reduction is carried out in the presence of a ligand and a catalyst to obtain the mepivacaine hydrochloride intermediate ((S)-N-(2, 6-dimethylphenyl) piperidine-2-carboxamide), the ee value of the obtained mepivacaine hydrochloride intermediate can reach 93%, the yield can reach 95%, post-treatment is simple, and the method is suitable for industrial production. The method is very suitable for large-scale workshop production. The ligand used in the invention is cheap and easily available, and can be refined and recovered through column chromatography, and the catalytic effect of the recovered ligand is consistent with that of a newly purchased ligand.

The invention discloses a novel C2 symmetric chiral bisamide ligand and a preparation method and application thereof, the ligand has a structure as shown in # imgabs0 #, Ar is aryl, the relative positions of two sulfur in the general formula are different, * represents a chiral center, R is 4-methylbenzyl, 4-bromobenzyl, 2, 6-dimethylbenzyl, methyl or benzyl, and n represents 1 or 2. Dithiophenol and (2S, 3S)-2, 3-diphenylaziridine react to obtain an intermediate, and the intermediate and nitrogen-substituted chiral cyclic amino acid or 2-diphenylphosphinobenzoic acid are subjected to dehydration condensation to obtain various ligands with novel structures. A catalyst formed by complexing the ligand and an allyl palladium chloride dimer can be used as a chiral ligand for efficiently catalyzing an asymmetric allyl alkylation reaction.

The present invention provides a [Ru(OAc)2(ligand)] catalyst of formula I, where R 1 is C 1~6 alkyl, and R 3 is hydrogen or C 1~6 alkyl, and R 4 is hydrogen or C 1~6 The [Ru(OAc)2(ligand)] catalyst is a versatile hydrogenation catalyst. TIFF2025525346000011.tif57128

This invention belongs to the field of organic synthesis technology and relates to a precursor of an obisec key intermediate and a method for preparing the key intermediate. The method involves a [4+2] cycloaddition reaction of 4-trifluoromethylaniline, propionaldehyde, and N-vinylformamide under the catalysis of chiral phosphoric acid, yielding the obisec key intermediate precursor with high enantioselectivity. N -((2) R 4 S )-2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinoline-4-yl)formamide; subsequently, the key intermediate of obisetri can be obtained through a deprotection reaction under acidic conditions. The method provided by this invention uses a small amount of chiral catalyst and commercially available reagents to efficiently obtain the key intermediate of obisetri in just two steps. R 4 S )-2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinoline-4-amine; under mild conditions without the need for chiral resolution, the utilization of starting materials is greatly improved, thereby significantly increasing the yield of the target product and the economic efficiency of the process.

The application provides a kind of plane chiral boronic acid compound based on cycloaralkane skeleton and its synthesis method and application, the plane chiral compound has the structure shown in formula I;R 1 It is selected from one of C1-C8 alkyl, C1-C8 alkoxy, C1-C20 aryloxy.R 2 It is selected from one of hydrogen, fluorine, methyl, ethyl, methoxy, ester group, nitro group, phenyl, benzyl, tert-butyl, isopropyl.The application can effectively synthesize plane chiral boronic acid catalyst based on cycloaralkane skeleton, and the plane chiral boronic acid catalyst based on cycloaralkane skeleton can realize diol desymmetrization reaction.

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 application discloses a kind of solid supported manganese catalyst and its preparation method and application, the preparation process of the catalyst includes complexing organic ligand with metal manganese salt, forms catalytic active unit, and then polymerizes with comonomer, obtains the solid supported manganese catalyst as shown in formula I or II.The solid supported manganese catalyst belongs to heterogeneous chiral catalyst, with higher catalytic activity and excellent enantioselectivity (ee value is as high as 98.3%), because it is insoluble in reaction solvent, easy to separate and recover with reaction system, with good stability.And it can be combined with continuous flow catalysis, maintain high catalytic activity for a long time, can be applied in the asymmetric epoxidation reaction of alpha, beta-unsaturated carbonyl compound.

Provided is a method for efficiently producing a fluorinated alkyl compound by directly converting an aliphatic alkylamine widely existing in nature into a fluorine substituent, the method being characterized in that an alkylamine compound in which at least one amino group is bonded to an alkyl carbon is reacted with a deamination-fluorination agent to produce the fluorinated alkyl compound.

The invention discloses an efficient synthesis method of ephedrine hydrochloride, and belongs to the technical field of pharmaceutical chemistry synthesizing.A self-synthesized chiral zinc oxide nanoflower composite catalyst is added in the synthesis process of the ephedrine hydrochloride, and the composite catalyst has a chiral function, is large in pore and surface area, easy to recover and not prone to blockage, and can be used for preparing a chiral zinc oxide nanoflower catalyst. Compared with a traditional Lewis acid type catalyst, the catalyst has the advantages that keto groups in ephedrine hydrochloride synthesis can be precisely reduced, and hexadecyl trimethyl ammonium bromide is intercalated on the surface, so that the catalyst is not easy to agglomerate in a catalytic system, and the yield of a product is further improved; according to the composite catalyst, through hexadecyl trimethyl ammonium bromide, the surface hydrophilicity and hydrophobicity of the composite catalyst are regulated and controlled, the composite catalyst is dispersed more uniformly and makes contact with a compound II more sufficiently, the speed and selectivity of a reductive amination reaction are improved, and the hexadecyl trimethyl ammonium bromide can intercalate mica lamellas, so that the mica lamellas are peeled off, the interlayer spacing is increased, and therefore the composite catalyst is more stable in performance. And the reaction sites are increased, so that the catalytic active center is loaded more stably.

The application belongs to the technical field of organic chemical synthesis, and particularly relates to a nitrogen center chiral base derivative, a preparation method and application thereof. The preparation method of the nitrogen center chiral base derivative provided by the application can effectively synthesize a base with only a nitrogen chiral center by using a tetrahydrodibenzo-diazocine compound as a raw material and through chiral phosphoric acid catalyzed amination reaction. Moreover, the synthesis method provided by the application has the advantages of high efficiency, simple steps and strong enantioselectivity, is suitable for industrialized production of chiral bases and derivatives thereof, and provides a new approach for research and application of chiral compounds. Meanwhile, the base derivative prepared by the application is a base molecule with a nitrogen center chirality, and has wide application prospects in the fields of molecular recognition, DNA binding, supramolecular chemistry, material science, asymmetric catalysis and drug development.

The invention relates to the technical field of organic luminescence, and discloses a binaphthylamine derivative as well as a preparation method and application thereof. According to the organic compound based on the binaphthylamine derivative, a series of D-A structure molecules are synthesized by taking a binaphthylamine-containing group as a donor structure and connecting different diphenyl sulfone derivative receptors, and the organic compound has relatively high quantum yield and can be applied to the fields of organic electroluminescent devices, fluorescent probes, asymmetric catalysis, information storage and the like.

The invention provides a preparation method of a novel chiral thiourea / phosphine bifunctional organic catalyst with a cis-cyclic 1, 2-phosphinamine skeleton and application of the novel chiral thiourea / phosphine bifunctional organic catalyst in an asymmetric catalytic reaction. The chiral organic catalyst is prepared by taking cis chiral 2-(diphenylphosphine)-1, 2, 3, 4-tetrahydro-1-naphthylamine and an isothiocyanate compound as raw materials through a one-step reaction under a mild condition. The chiral thiourea / phosphine bifunctional organic catalyst is simple to prepare and stable in property, and shows excellent catalytic activity and stereoselectivity in an asymmetric hydrosilylation reaction of o-amido benzophenone.