10 results about "Chiral diamine" patented technology

The invention relates to the field of asymmetric catalytic hydrogenation, in particular to an asymmetric hydrogenation kinetic resolution method of racemic polysubstituted three-membered ring imine, which is characterized by comprising the following steps: in the presence of a chiral diamine metal catalyst, carrying out asymmetric hydrogenation kinetic resolution on racemic polysubstituted three-membered ring imine; the method comprises the following steps: carrying out asymmetric hydrogenation treatment on a mixture containing enantiomers of the multi-substituted three-membered cyclic imine compound by adopting hydrogen to obtain a single optical isomer of the multi-substituted chiral aziridine compound and / or the multi-substituted chiral three-membered cyclic imine compound; wherein the polysubstituted three-membered cyclic imine compound is a compound as shown in a formula (1), and the polysubstituted chiral aziridine compound is a compound as shown in a formula (2). According to the method disclosed by the invention, the resolution of the racemic polysubstituted three-membered cyclic imine compound is realized in an asymmetric hydrogenation manner, and a polysubstituted chiral aziridine compound with certain optical purity and a single optical isomer of the polysubstituted chiral three-membered cyclic imine compound can be obtained at the same time.

The invention relates to a preparation method of a diamine chiral resolving agent. The method comprises the following steps: by taking chiral alpha-amino acid as a raw material, reacting the chiral alpha-amino acid with (Boc) 2O and alkali in a solvent to obtain Boc-protected amino acid; in a solvent, the Boc-protected amino acid and secondary amine are subjected to catalysis of a condensing agent and alkali to obtain Boc amino-protected secondary amide; dissolving the Boc amino protected secondary amide in an organic solvent, and removing a Boc protecting group under an acidic condition to obtain chiral alpha-amino secondary amide; and reducing the chiral alpha-amino secondary amide into amine under the action of a reducing agent to obtain chiral amino secondary amine, namely the target product diamine chiral resolving agent. The chiral alpha-amino acid required by the preparation method is cheap and easy to obtain, the operation is simple, the obtained chiral diamine resolving agent is novel in structure, the variety of alkaline resolving agents is enriched, and the chiral diamine resolving agent is applied to resolution of racemic propionic acid compounds such as non-steroidal anti-inflammatory drugs ibuprofen and flurbiprofen and has practicability.

The invention discloses a method for preparing a chiral amine compound through asymmetric hydrogenation of ruthenium catalyzed imine. The chiral ruthenium catalyst is a chiral metal ruthenium complex prepared by reacting metal ruthenium salt with a chiral phosphine-phosphoramidite ester ligand and chiral diamine in a solvent and carrying out column chromatography. Compared with other chiral amine synthesis methods, the method provided by the invention has the characteristics of cheap catalyst, easy preparation of chiral ligand, mild reaction conditions, simple operation, high yield and enantioselectivity and the like, and can be applied to large-scale preparation of chiral amine compounds. The method is also suitable for synthesis of the key intermediate of the herbicide (S)-metolachlor, the yield can reach 92%, the enantioselectivity can reach 90%, and the method has good industrial application prospects.

The present application relates to a kind of chiral six-tooth nitrogen-containing binuclear ligand, the present application is first synthesized chiral diamine as parent skeleton, the binuclear chiral ligand containing pyridine and chiral oxazoline unit, use chiral diamine as chiral skeleton to tie two pyridine oxazoline groups, wherein chiral diamine and chiral oxazoline unit have (S) or (R) configuration chiral center carbon.The synthesis method of ligand is obtained by five steps or six steps reaction with simple available raw materials.The ligand is functional ligand, can be able to with two same or different metal coordination, in reaction binuclear jointly activates substrate or mononuclear activates substrate, another metal as ligand influences catalytic center activity.This kind of binuclear catalyst is expected to realize the reaction that conventional mononuclear catalyst is difficult to realize by unique metal-metal bond, and be applied to many asymmetric catalytic reactions, with good application prospect.

The invention discloses a chiral spiro compound and a preparation and use method thereof. In particular, provided are spiro compounds useful as chiral ligands and chiral organic catalysts, including chiral spiro diamines, chiral spiro aminonaphthol, chiral spiro bis (indole), chiral spiro diaryl diol, chiral spiro diaryl diamines, chiral spiro aminonaphthol, chiral spiro diaryl diindole, and chiral spiro phosphoropentane. Due to molecular shape and three-dimensional orientation, chiral diamine and chiral aminonaphthol molecules provide backbones for use as ligands and organocatalysts.

The invention relates to a resolution method of a chiral drug, in particular to a resolution method of an (S)-propionic acid non-steroidal anti-inflammatory drug. The method comprises the following steps: by taking a racemic propionic acid non-steroidal anti-inflammatory drug as a raw material and chiral diamine as a resolving agent, reacting in a solvent under the action of a stabilizer to obtain diastereomer salt; recrystallizing the obtained diastereomer salt with a solvent to further improve the purity; acidifying the purified diastereomer, and filtering or extracting with an organic solvent to obtain a crude product of the (S)-propionic acid non-steroidal anti-inflammatory drug; and completely dissolving the (S)-propionic acid non-steroidal anti-inflammatory drug crude product with a benign solvent, adding a poor solvent, and recrystallizing to obtain the (S)-propionic acid non-steroidal anti-inflammatory drug with high optical purity. The resolving agent needed by the preparation method is novel, the resolving effect is good, the enantiomeric excess is larger than or equal to 95.0%, the yield is high, operation is easy, and amplification feasibility is achieved.

This invention provides an ultra-chiral covalent organic framework, its preparation method, and its applications, belonging to the field of chiral covalent organic framework materials. It aims to solve the technical problem of racemization of chiral signals caused by existing high-temperature synthesis methods. First, a C3-symmetric aldehyde monomer is reacted with a chiral monoamine in an alcohol solvent to generate a 1:1 precursor molecule. Then, an achiral diamine is added, and ligand exchange and chiral transfer are performed at room temperature to form a trilobal propeller-structured macromolecule with pure uniform chirality. Finally, long-range conjugation and crystallization are completed via a water bath or air bath, followed by washing and drying to obtain the target product. The obtained material exhibits ultra-high chiral signal, with a circular dichroism spectral signal intensity CD≈±2,000 mdeg and an asymmetry factor g. abs The chiral stability reached ±0.085, and a cascade chiral amplification effect of up to 200-fold was observed. Furthermore, the material exhibited excellent chiral stability, maintaining its stability for at least 5 years. In addition, it can be used as a recognition reagent, capable of distinguishing at least seven pairs of amino acid enantiomers and five other small molecule enantiomers.

This invention discloses a method for preparing triarylmethanes via an asymmetric photochemical reaction of chiral primary amine-catalyzed pyridinetriazole and boric acid, belonging to the field of organic synthesis. This application develops a highly efficient modular asymmetric photochemical strategy, with the following synthetic route: The chiral catalyst used is one of C1-C9, with the following structural formulas: Using pyridinetriazole (Formula I) and boric acid (Formula II) as substrates, and employing novel chiral diamine-derived pyrroles or primary amines as catalysts, this application successfully and efficiently synthesized a variety of triarylmethanes with high yields and high enantioselectivity. This method not only demonstrates broad substrate applicability and excellent functional group tolerance, but also utilizes inexpensive D₂O as a deuterium source to precisely synthesize a series of deuterated derivatives, providing an efficient and economical route for synthesizing high-value molecules containing chiral C–D bonds.

The invention belongs to the field of synthetic chemistry and biological medicine, and particularly relates to a difluoromethyl modified chiral diamine derivative as well as a synthetic method and application thereof. The difluoromethyl modified chiral diamine derivative is obtained by taking p-toluenesulfonyl difluoromethyl diazomethane, aromatic amine, organic aldehyde and electron-rich aromatic hydrocarbon as raw materials and taking chiral phosphoric acid as a chiral inducer and an organic reagent as a solvent through a one-step reaction under the catalysis of transition metal. According to the difluoromethyl modified chiral diamine derivative and the synthesis method, the raw materials are cheap and easy to obtain, safe and non-toxic, the reaction condition is mild, the operation is simple and safe, and the synthesized difluoromethyl modified chiral diamine derivative has good anti-tumor activity and has huge development potential in the field of drug research and development.

The present application relates to the technical field of organic synthesis, and particularly relates to a kind of boron-containing chiral allyl ester compound and high stereoselective synthesis method, comprising the following steps: under the action of catalyst, chiral diamine ligand and base, acetylene, boron reagent and alkyl bromide are dissolved in organic solvent and are reacted, and boron-containing chiral allyl ester compound is obtained by separation and purification.The method of the present application uses acetylene, alkyl bromide and double boron reagent, and boron-containing chiral allyl ester compound is prepared by one-step reaction under the synergistic effect of catalyst and diamine ligand, which can not only efficiently synthesize target compound, but also has mild reaction condition, strong substrate universality, good functional group compatibility, excellent chemical selectivity and stereoselectivity, and the highest ee value can reach 95%, the raw materials used are cheap and easy to obtain, and the operation is simple, so that boron-containing chiral allyl ester compound can be efficiently synthesized.