CN117486707A - Synthesis method of diene ligand with chiral bicyclo [2.2.2] skeleton - Google Patents
Synthesis method of diene ligand with chiral bicyclo [2.2.2] skeleton Download PDFInfo
- Publication number
- CN117486707A CN117486707A CN202310483461.8A CN202310483461A CN117486707A CN 117486707 A CN117486707 A CN 117486707A CN 202310483461 A CN202310483461 A CN 202310483461A CN 117486707 A CN117486707 A CN 117486707A
- Authority
- CN
- China
- Prior art keywords
- diene
- chiral
- synthesizing
- ligands
- ligand
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001993 dienes Chemical class 0.000 title claims abstract description 58
- 239000003446 ligand Substances 0.000 title claims abstract description 46
- 238000001308 synthesis method Methods 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 8
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- 238000007115 1,4-cycloaddition reaction Methods 0.000 claims abstract description 3
- 238000005859 coupling reaction Methods 0.000 claims abstract description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 239000007818 Grignard reagent Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- 150000004795 grignard reagents Chemical class 0.000 claims description 2
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 9
- 238000003786 synthesis reaction Methods 0.000 abstract description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 230000003335 steric effect Effects 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- -1 diene compound Chemical class 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000012512 characterization method Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical group CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 3
- 239000001169 1-methyl-4-propan-2-ylcyclohexa-1,4-diene Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/325—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/44—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing eight carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention relates to a method for synthesizing diene ligands with chiral bicyclo [2.2.2] frameworks. Efficient and simple synthesis of chiral ligands with a variety of functional groups has been one of the important research points in the field of asymmetric catalysis. The project aims at synthesizing diene bodies with various substituents through a copper-catalyzed coupling reaction, further carrying out [4+2] cycloaddition with dienophiles, synthesizing chiral diene racemates with [2.2.2] and [3.2.2] frameworks through reaction, further converting into carboxylic acid derivatives of diene ligands, and obtaining a pair of optically active chiral diene ligands through a chemical resolution means. The ligand can be further simply and efficiently converted into a series of chiral mixed phosphine, oxy-alkene or thio-alkene ligands with different electronic effects and steric effects.
Description
Technical Field
The invention belongs to the technical field of synthesis of organic compounds, and discloses a synthesis method of a diene ligand with a chiral bicyclo [2.2.2] skeleton.
Background
It is well known that the enantioselectivity of asymmetric catalytic reactions is largely dependent on chiral catalysts, where chiral ligands are the root cause of the induction of optically active products. Compared with the early chiral diene ligand of the [2.2.1] framework, the chiral diene ligand of the [2.2.2] framework is a focus of research on the chiral diene ligand due to the stability of the chiral diene ligand.
The literature studies and our previous work have shown that chiral diene ligands ((R, R) -V) of the [2.2.2] backbone prepared from commercial optically pure (R) -phellandrene have excellent enantioselectivity and induction of reactivity in a series of asymmetric catalytic reactions [ Okamoto, k.; hayashi, t.; rawal, v.h. org.lett.2008 10, 4387-4389. However, such ligands have the following limitations: 1) Limited to the preparation of (S) -phellandrene, the enantiomer ((S, S) -V) of the chiral diene ligand ((R, R) -V) is not readily available, resulting in insufficient investigation and exploration of the biological or pharmacological activity of one of the enantiomers of the compound of interest; 2) The olefinic methyl moiety in the non-C2 symmetric chiral diene ligand ((R, R) -V) is not easily modified.
Therefore, the synthesis of a new chiral ligand based on the [2.2.2] skeleton of chiral diene ligand ((R, R) -V) has important academic and practical significance.
Disclosure of Invention
This section is intended to outline some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. Some simplifications or omissions may be made in this section as well as in the description summary and in the title of the application, to avoid obscuring the purpose of this section, the description summary and the title of the invention, which should not be used to limit the scope of the invention.
The present invention has been made in view of the above and/or problems occurring in the prior art.
Therefore, the invention aims to overcome the defects in the prior art and provide a method for synthesizing a diene ligand with a chiral bicyclo [2.2.2] skeleton.
In order to solve the technical problems, the invention provides the following technical scheme: a method for synthesizing a diene ligand of a chiral bicyclo [2.2.2] skeleton comprises the steps of,
synthesizing diene bodies with various substituents through a copper-catalyzed coupling reaction, performing [4+2] cycloaddition with dienophile bodies, synthesizing diene racemate with a [2.2.2] framework through reaction, further converting into carboxylic acid derivatives of diene ligands, and obtaining a pair of optically active chiral diene ligands through a chemical resolution method.
The synthesis method of the diene ligand of the chiral bicyclo [2.2.2] skeleton is characterized in that: the copper catalyst used was CuI in an amount of 10% of the diene
The synthesis method of the diene ligand of the chiral bicyclo [2.2.2] skeleton is characterized in that: the diene bodies of the various substituents are obtained by reacting a trifluoro methanesulfonyl substituted diene body with a Grignard reagent at a low temperature under the catalysis of copper.
The synthesis method of the diene ligand of the chiral bicyclo [2.2.2] skeleton is characterized in that: the dienophile is commercially available methyl propiolate.
The synthesis method of the diene ligand of the chiral bicyclo [2.2.2] skeleton is characterized in that: the carboxylic acid derivative of the diene ligand is obtained by reacting a diene raceme of a [2.2.2] framework with water and hydrochloric acid.
The synthesis method of the diene ligand of the chiral bicyclo [2.2.2] skeleton is characterized in that: after the diene ligand is obtained, further chemical resolution can be performed to obtain a series of different ligands which are enantiomers.
The invention has the beneficial effects that:
the method is simple and easy to operate, and the required products in the method have the advantages of low toxicity, safety, environmental protection, wide subsequent conversion range, high yield and high reaction efficiency. The invention uses raw materials and catalysts which are all commercially available, a pair of chiral diene ligands with optical activity can be obtained through a series of reactions under mild conditions, and various subsequent conversions can be carried out.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings that are needed in the description of the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art. Wherein:
FIG. 1 is a chart showing the hydrogen nuclear magnetic resonance spectrum of the product prepared in example 1 of the present invention;
FIG. 2 is a chart showing the nuclear magnetic resonance spectrum of the product prepared in example 1 of the present invention;
FIG. 3 is a flow chart of the products prepared in examples 1-6 of the present invention.
Detailed Description
In order that the above-recited objects, features and advantages of the present invention will become more apparent, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways other than those described herein, and persons skilled in the art will readily appreciate that the present invention is not limited to the specific embodiments disclosed below.
Further, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic can be included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
Example 1
The synthesis of the isopropylbenzene substituted diene compound comprises the following steps:
a10 ml reaction flask was placed with a stirrer, and 10% cuprous iodide, 1.2eq isopropyl benzene grignard reagent and 1mmol triflylcyclohexadiene were placed in the flask. Under nitrogen, 1.2 ml THF was added to the reaction flask. Stirring at low temperature for 16h.
Characterization of the product: 1 H NMR(CDCl3，600MHz)δ1.21(d，J＝6.9Hz，6H)，2.21-2.27(m，2H)，2.30-2.36(m，2H)，3.15-3.22(m，1H)，5.70(t，1H)，5.88-5.92(m，1H)，5.95-5.98(m，1H)，7.09-7.11(m，1H)，7.13-7.17(m，1H)，7.25-7.32(m，2H). 13 C NMR(CDCl3，151MHz)δ21.9，22.7，24.2，29.6，124.2，125.3，125.4，125.8，127.3，128.2，129.0，137.3，141.3，146.5
the structural formula of the product is as follows:
example 2
The synthesis of the cumene-substituted diene racemate proceeds as follows:
a10 ml reaction flask was charged with a stirrer, and the isopropylbenzene-substituted diene compound obtained in example I was placed in the flask. Under the protection of nitrogen, 1eq of dimethylaluminum chloride and methylene chloride are added into a reaction bottle in sequence. Stirring at low temperature for 6h.
Characterization of the product: 1 H NMR(CDCl3，600MHz)δ1.12(d，J＝6.8Hz 3H)，1.25(d，J＝6.9Hz，3H)，1.38-1.49(m，2H)，1.51-1.66(m，2H)，2.92-2.99(m，1H)，3.79(s，1H)，4.29-4.31(m，1H)，6.20-6.22(m，1H)，6.99-7.01(m，1H)，7.11-7.15(m，1H)，7.24-7.31(m，2H)，7.45-7.47(m，1H). 13 C NMR(CDCl3，151MHz)δ23.9，24.3，24.4，25.1，29.7，36.9，44.4，51.5，125.3，125.4，127.5，128.6，130.7，138.7，139.2，145.4，146.3，146.6，165.4.
the structural formula of the product is as follows:
example 3
The synthesis of carboxylic acid derivatives of cumene-substituted diene ligands proceeds as follows:
a10 ml reaction flask was charged with a stirrer, and the cumene-substituted diene racemate obtained in example II was placed in the flask. Under the protection of nitrogen, water and 1N HCl are added into a reaction bottle in sequence. Stirring at high temperature for 6h, and characterizing the product: 1 H NMR(CDCl 3 ，600MHz)δ1.12(d，J＝6.8Hz 3H)，1.26(d，J＝6.8Hz，3H)，1.40-1.50(m，2H)，1.53-1.65(m，2H)，2.91-2.98(m，1H)，3.86-3.88(m，1H)，4.29-4.31(m，1H)，6.22-6.24(m，1H)，7.01-7.02(m，1H)，7.12-7.16(m，1H)，7.25-7.32(m，2H)，7.62-7.65(m，1H). 13 C NMR(CDCl 3 ，151MHz)δ24.0，24.3，24.4，25.1，29.8，36.7，44.7，125.4，125.5，127.6，128.6，130.7，138.6，138.9，146.2，146.7，148.5，170.3
the structural formula of the product is as follows:
example 4
The synthesis of toluene-substituted diene compounds is as follows:
a10 ml reaction flask was placed with a stirrer, and 10% cuprous iodide, 1.2eq toluene grignard reagent and 1mmol triflylcyclohexadiene were placed in the flask. Under nitrogen, 1.2 ml THF was added to the reaction flask. Stirring at low temperature for 16h. The process is as follows:
characterization of the product: 1 H NMR(CDCl 3 ，600MHz)δ2.21-2.28(m，2H)，2.32-2.38(m，5H)，5.73-5.76(m，1H)，5.91-5.95(m，1H)，5.98-6.02(m，1H)，7.15-7.20(m，4H). 13 C NMR(CDCl 3 ，151MHz)δ20.1，21.9，22.6，124.3，125.6，126.0，126.8，127.7，128.5，130.0，135.4，137.2，142.0.
the structural formula of the product is as follows:
example 5
The synthesis of toluene-substituted diene racemate is as follows:
a10 ml reaction flask was charged with a stirrer, and the toluene-substituted diene compound obtained in example I was placed in the flask. Under the protection of nitrogen, 1eq of dimethylaluminum chloride and methylene chloride are added into a reaction bottle in sequence. Stirring at low temperature for 6h.
Characterization of the product: 1 H NMR(CDCl 3 ，600MHz)δ1.39-1.63(m，4H)，2.26(s，3H)，3.79(s，3H)，3.89-3.92(m，1H)，4.30-4.33(m，1H)，6.26-6.28(m，1H)，7.06-7.11(m，1H)，7.13-7.19(m，3H)，7.46(dd，J＝1.87，6.39Hz，1H). 13 C NMR(CDCl 3 ，151MHz)δ20.6，24.4，25.2，36.9，43.6，51.5，125.7，127.1，128.2，130.3，131.3，135.5，139.4，139.4，145.6，146.4，165.4
the structural formula of the product is as follows:
example 6
The synthesis of carboxylic acid derivatives of toluene-substituted diene ligands proceeds as follows:
a10 ml reaction flask was placed with a stirrer, and the toluene-substituted diene racemate obtained in example II was placed in the flask. Under the protection of nitrogen, water and 1N HCl are added into a reaction bottle in sequence. Stirring at high temperature for 6h.
Characterization of the product: h NMR (CDCl) 3 ，600MHz)δ1.41-1.66(m，4H)，2.26(s，3H)，3.94(d，J＝6.1Hz，3H)，4.31(d，J＝6.1Hz，1H)，6.29(d，J＝6.3Hz，1H)，7.08-7.09(m，1H)，7.14-7.20(m，3H)，7.64(d，J＝6.4Hz，1H). 13 C NMR(CDCl 3 ，151MHz)δ20.6，24.3，25.2，36.6，43.8，125.7，127.1，128.2，130.4，131.3，135.5，139.0，139.3，146.2，148.6，170.2.
The structural formula of the product is as follows:
it should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the same, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the technical solution of the present invention may be modified or substituted without departing from the spirit and scope of the technical solution of the present invention, which is intended to be covered in the scope of the claims of the present invention.
Claims (6)
1. A method for synthesizing a diene ligand with a chiral bicyclo [2.2.2] skeleton comprises the following steps: the method aims at synthesizing diene bodies with various substituents through a copper-catalyzed coupling reaction, so that [4+2] cycloaddition is carried out on the diene bodies, diene racemates with [2.2.2] frameworks are synthesized through reaction, carboxylic acid derivatives of diene ligands are further converted, and then a pair of optically active chiral diene ligands are obtained through a chemical resolution means.
2. A method for synthesizing a diene ligand having a chiral bicyclo [2.2.2] skeleton according to claim 1, wherein: the copper catalyst used was CuI, which was used in an amount of 10% of the diene.
3. A method for synthesizing a diene ligand having a chiral bicyclo [2.2.2] skeleton according to claim 1, wherein: the diene bodies of various substituents are obtained by the reaction of a trifluoro methanesulfonyl substituted diene body and a Grignard reagent at a low temperature under the catalysis of copper.
4. A method for synthesizing a diene ligand having a chiral bicyclo [2.2.2] skeleton according to claim 1, wherein: the dienophile is commercially available methyl propiolate.
5. A method for synthesizing a diene ligand having a chiral bicyclo [2.2.2] skeleton according to claim 1, wherein: the carboxylic acid derivative of the diene ligand is obtained by reacting a diene raceme of a [2.2.2] framework with water and sodium hydroxide.
6. A method for synthesizing a diene ligand having a chiral bicyclo [2.2.2] skeleton according to claim 1, wherein: the carboxylic acid derivative of the diene ligand can be subjected to further chemical resolution to obtain a series of chiral diene ligands which are enantiomers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310483461.8A CN117486707A (en) | 2023-04-28 | 2023-04-28 | Synthesis method of diene ligand with chiral bicyclo [2.2.2] skeleton |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310483461.8A CN117486707A (en) | 2023-04-28 | 2023-04-28 | Synthesis method of diene ligand with chiral bicyclo [2.2.2] skeleton |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117486707A true CN117486707A (en) | 2024-02-02 |
Family
ID=89678838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310483461.8A Pending CN117486707A (en) | 2023-04-28 | 2023-04-28 | Synthesis method of diene ligand with chiral bicyclo [2.2.2] skeleton |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117486707A (en) |
-
2023
- 2023-04-28 CN CN202310483461.8A patent/CN117486707A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109734666B (en) | Preparation method for synthesizing indazolinones compound by carbon dioxide promotion and photo-induction without photocatalyst | |
| CN112724058B (en) | Synthesis method of visible light-promoted beta-hydroxyselenide compound | |
| CN107955183A (en) | A kind of coordination polymer with light reaction and preparation method thereof | |
| JP2962668B2 (en) | Method for producing optically active alcohols | |
| CN110305054A (en) | A kind of preparation method of disubstituted benzene vinyl derivatives | |
| Periasamy et al. | Synthesis of Amines by Reduction of Imines with the MCl2/NaBH4 (M= Co, Ni) System | |
| CN117486707A (en) | Synthesis method of diene ligand with chiral bicyclo [2.2.2] skeleton | |
| CN112851538B (en) | Method for promoting acylation of amine or alcohol by carbon dioxide | |
| CN109942418A (en) | The preparation method of compound and chipal compounds | |
| CN110317170B (en) | Green synthesis method of 3-phenanthridinyl propyl formate compound | |
| CN113735752A (en) | Method for preparing isothiourea compound based on substituted iodobenzene | |
| CN108948055B (en) | 8-methylquinoline gem-diboron compound and preparation method thereof | |
| CN111393869A (en) | Fluorescent dye containing phenylethynyl naphthalene, preparation method and application thereof | |
| CN111217693A (en) | method for preparing a, β -unsaturated carboxylic acid by reacting alkenyl boron compound catalyzed by cuprous halide with carbon dioxide | |
| CN111793040B (en) | Preparation method of 2-substituted benzothiazole | |
| CN111635312B (en) | Synthesis method of (E) -2-fluoroalkyl-3-butenoate compound | |
| CN111848673A (en) | Cyclohexyl fused ring spiroindane diphosphine ligand | |
| CN114213443B (en) | Method for preparing alkyl boron ester from alkenyl boron ester | |
| CN114874105B (en) | Preparation method of visible light and water promoted homoallylic amine compound | |
| CN115650824B (en) | Chiral diol and preparation method thereof, prepared catalyst and preparation method and application thereof | |
| CN114773301B (en) | Method for synthesizing furan compounds from terminal alkyne and iodoylide | |
| CN113058652B (en) | Zirconium gallate catalyst and application thereof in selective hydrogenation reaction of crotonaldehyde | |
| CN117050011B (en) | Method for synthesizing 2-methylquinoline by using vinyl acetate as raw material | |
| CN115583874B (en) | Method for catalyzing asymmetric tandem reaction of internal alkyne by rhodium metal | |
| CN110862304B (en) | Method for synthesizing benzfluorene compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |