CN108864210A - The synthetic method of more hydrogen bond ferrocene catalyst - Google Patents
The synthetic method of more hydrogen bond ferrocene catalyst Download PDFInfo
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- CN108864210A CN108864210A CN201810741762.5A CN201810741762A CN108864210A CN 108864210 A CN108864210 A CN 108864210A CN 201810741762 A CN201810741762 A CN 201810741762A CN 108864210 A CN108864210 A CN 108864210A
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- 239000003054 catalyst Substances 0.000 title claims abstract description 28
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000001257 hydrogen Substances 0.000 title claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 11
- 238000010189 synthetic method Methods 0.000 title claims abstract description 8
- 230000021736 acetylation Effects 0.000 claims abstract description 7
- 238000006640 acetylation reaction Methods 0.000 claims abstract description 7
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 trifluoromethyl phenyl -1,2- ethylenediamine Chemical compound 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 238000006073 displacement reaction Methods 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 2
- 238000005712 Baylis-Hillman reaction Methods 0.000 abstract description 6
- 239000000758 substrate Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical group C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- 238000004296 chiral HPLC Methods 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- YNKMHABLMGIIFX-UHFFFAOYSA-N benzaldehyde;methane Chemical compound C.O=CC1=CC=CC=C1 YNKMHABLMGIIFX-UHFFFAOYSA-N 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- DGZXMSLLXBWIFG-UHFFFAOYSA-N formaldehyde;pyridine Chemical compound O=C.C1=CC=NC=C1 DGZXMSLLXBWIFG-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of synthetic methods of more hydrogen bond ferrocene catalyst, are starting material using optically pure (R)-N, N- dimethyl ferrocene ethamine, and lithiumation introduces diphenyl phosphine group later, then carries out acetylation, be finally introducing 1,2- diphenyl-N1Bis trifluoromethyl phenyl -1,2- ethylenediamine obtains final catalyst, and applies it to asymmetric Baylis-Hillman reaction.The method of the present invention high income, by-product is few, easy to operate, and catalyst activity is high, and substrate applicability is wide.
Description
Technical field
The present invention relates to asymmetric catalysis field is belonged to, be related to a kind of novel ferrocene catalyst design synthesis and its
Application in asymmetric Baylis-Hillman reaction is using optically pure (R)-N, N- dimethyl ferrocene ethamine
Beginning raw material, lithiumation introduce diphenyl phosphine group later, then carry out acetylation, be finally introducing 1,2- diphenyl-N1- bis trifluoromethyl
Phenyl -1,2- ethylenediamine obtains final catalyst, and applies it to asymmetric Baylis-Hillman reaction.Side of the present invention
Method high income, by-product is few, easy to operate, and catalyst activity is high, and substrate applicability is wide.
Background technique
Baylis-Hillman reaction generates the reaction with multiple molecule of functional group, Neng Gouman as C-C key is formed
Sufficient organic synthesis is for Atom economy and selectivity (including chemo-selective, regioselectivity, diastereomeric and mapping)
It is required that and its reaction condition it is mild, usually react at room temperature.The Baylis-Hillman reaction product of highly functionalized
Aziridine, epoxide etc., biologically active molecule and natural products can be converted into.But the reaction speed
Slowly, the reaction time is long, it usually needs and several days even reaction time in several weeks limit the selectivity of its reaction substrate, and
And asymmetric Baylis-Hillman reaction product ee value is lower, further limits the application of the reaction.In the recent period, largely
The range of choice that research work has been used to accelerate reaction speed, has extended reaction substrate, improves the corresponding selection of product.
Carretero seminar takes the lead in having attempted the asymmetric Baylis- that ferrocene phosphine is catalyzed acrylate and aldehyde
Hillma reaction, discovery ferrocene phosphine can effectively shorten time of reaction, improve the yield of reaction, but the ee value of product
Only 65%, reaction equation is：
。
Hayashi seminar is using proline as raw material, synthesis of chiral Diamines catalyst, for being catalyzed methyl vinyl ketone
The asymmetric B-H participated in aromatic aldehyde reacts, and product ee value is up to 75%.Meanwhile Rouden and Maddaluno are also with pyrroles
Alkane be parent prepare chiral diamine class catalyst, however, reaction corresponding selection be not it is too ideal, product ee value be 44-
75%, and the reaction time is up to 8 days, and reaction equation is：
。
Later, Zhao, Zhou et al., synthesis one is class alkamine chiral catalyst, with L-PROLINE co-catalysis
Aromatic aldehyde and α, the B-H reaction of alpha, beta-unsaturated ketone, product corresponding selection is only 31-83%, and the reaction time is longer, reaches 8-10
It.
Summary of the invention
The object of the present invention is to provide a kind of synthetic methods of more hydrogen bond ferrocene catalyst, how solve to more hydrogen bonds two
The technical issues of luxuriant iron catalyst is synthesized.
The synthetic method of more hydrogen bond ferrocene catalyst, includes the following steps：
Optically pure (R)-N, N- dimethyl ferrocene ethamine 1g is added in tri- mouthfuls of reaction flasks of 100mL by a, be added solvent just oneself
Alkane 30mL carries out argon gas displacement, is subsequently placed in -78 DEG C of low-temperature reactors, the tert-butyl lithium of 1.2eq is added, is then added
1.1eq Chlorodiphenylphosphine, obtains yellow solid after reaction；
Yellow solid i.e. (R) -1- (2- diphenylphosphine)-N, N- dimethyl ferrocene ethamine that reaction obtains is added to 50mL by b
10mL aceticanhydride is added in single port bottle, is heated to 60-100 DEG C, reacts 6h-10h, generates the product of acetylation；
The product of acetylation is added to (1R, 2S) -1,2- diphenyl-N1- bis trifluoromethyl phenyl -1,2- ethylenediamine by c
In dichloromethane solution, 25-60 DEG C of reaction 8h；Reaction equation is：
。
In the step a, hexane solution must carry out pretreated anhydrous solvent.
In the step c, reaction must carry out under conditions of anhydrous and oxygen-free.
The beneficial effects of the invention are as follows：The each step reaction yield of the present invention is all higher, can quantitatively complete, after being not necessarily to
Reason can be directly thrown into reaction in next step, and final product can be obtained by simple column chromatography.By using described above
Catalyst compared with existing catalyst, beneficial effects of the present invention are as follows：Use ferrocene simple and easy to get for raw material, benefit
There is the design feature of face chirality and central chirality with ferrocene, more hydrogen bond new catalysts are prepared in design, and the catalyst is not
The rate of reaction only can be improved, and can effectively improve the corresponding selection of product, reaction condition is mild, and it is easy to operate,
Utilize large-scale application.
Specific embodiment
The synthesis of more hydrogen bond ferrocene catalyst of the invention, first with optically pure (R)-N, N- dimethyl ferrocene second
Amine is starting material, and lithiumation is reacted with Chlorodiphenylphosphine later, then carries out acetylation, finally with optically pure (1R, 2S)-
1,2- diphenyl-N1- bis trifluoromethyl phenyl -1,2- reacting ethylenediamine obtains catalyst.
The specific reaction equation of the present invention is as follows：
。
Embodiment 1
Resulting catalyst 25mg is weighed, is added in 15mL tube sealing, toluene solvant 5mL is added, the benzene of 500mg is then added
The methyl acrylate of formaldehyde and 2mL was directly spin-dried for column after reacting at room temperature 86h, finally obtained white solid, yield 73%, warp
Chiral HPLC is crossed, product ee value is 92%, and specific reaction is as follows：
。
Embodiment 2
Resulting catalyst 25mg is weighed, is added in 15mL tube sealing, THF solvent 5mL is added, the acetaldehyde of 130mg is then added
With the cyclohexyl -2- ketenes of 2mL, it was directly spin-dried for column after reacting at room temperature 72h, finally obtains white solid, yield 70%, warp
Chiral HPLC is crossed, product ee value is 94%, and specific reaction is as follows：
。
Embodiment 3
Resulting catalyst 25mg is weighed, is added in 15mL tube sealing, toluene solvant 5mL is added, pair of 520mg is then added
The methyl acrylate of tolyl aldehyde and 2mL was directly spin-dried for column after reacting at room temperature 100h, and finally obtained white solid, yield
It is 67%, by chiral HPLC, product ee value is 89%.
Embodiment 4
Resulting catalyst 25mg is weighed, is added in 15mL tube sealing, toluene solvant 5mL is added, pair of 560mg is then added
The methyl acrylate of fluorobenzaldehyde and 2mL was directly spin-dried for column after reacting at room temperature 69h, and finally obtained white solid, yield is
77%, by chiral HPLC, product ee value is 91%.
Embodiment 5
Resulting catalyst 25mg is weighed, is added in 15mL tube sealing, chlorobenzene solvent 5mL is added, the pyrrole of 530mg is then added
The methyl acrylate of pyridine formaldehyde and 2mL was directly spin-dried for column after reacting at room temperature 120h, and finally obtained white solid, yield is
79%, by chiral HPLC, product ee value is 82%.
Claims (3)
1. the synthetic method of the ferrocene catalyst of hydrogen bond more than, includes the following steps：It is characterized in that：A by optically pure (R)-N,
N- dimethyl ferrocene ethamine 1g is added in tri- mouthfuls of reaction flasks of 100mL, and solvent hexane 30mL is added, and carries out argon gas displacement,
It is subsequently placed in -78 DEG C of low-temperature reactors, the tert-butyl lithium of 1.2eq is added, 1.1eq Chlorodiphenylphosphine is then added, instead
Yellow solid is obtained after answering；
Yellow solid i.e. (R) -1- (2- diphenylphosphine)-N, N- dimethyl ferrocene ethamine that reaction obtains is added to 50mL by b
10mL aceticanhydride is added in single port bottle, is heated to 60-100 DEG C, reacts 6h-10h, generates the product of acetylation；
The product of acetylation is added to (1R, 2S) -1,2- diphenyl-N1- bis trifluoromethyl phenyl -1,2- ethylenediamine by c
In dichloromethane solution, 25-60 DEG C of reaction 8h；Reaction equation is：
。
2. the synthetic method of more hydrogen bond ferrocene catalyst according to claim 1, it is characterised in that：The step a
In, hexane solution must carry out pretreated anhydrous solvent.
3. the synthetic method of more hydrogen bond ferrocene catalyst according to claim 1, it is characterised in that：The step c
In, reaction must carry out under conditions of anhydrous and oxygen-free.
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| CN201810741762.5A CN108864210A (en) | 2018-07-09 | 2018-07-09 | The synthetic method of more hydrogen bond ferrocene catalyst |
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| CN201810741762.5A CN108864210A (en) | 2018-07-09 | 2018-07-09 | The synthetic method of more hydrogen bond ferrocene catalyst |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109078653A (en) * | 2018-10-08 | 2018-12-25 | 浙江工业大学上虞研究院有限公司 | Chiral ferrocene phosphoric acid catalyst and its application in asymmetric Friedel-Crafts reaction |
| CN114853820A (en) * | 2022-05-13 | 2022-08-05 | 江苏医药职业学院 | Ferrocene and camphorsulfonic acid composite derivative, preparation method thereof and application thereof in catalyzing asymmetric P-S reaction |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103831133A (en) * | 2014-02-25 | 2014-06-04 | 中国人民解放军第四军医大学 | Bi-functional phosphine thiourea organic catalyst based on ferrocene skeleton as well as preparation method and application thereof |
| CN107722068A (en) * | 2017-11-09 | 2018-02-23 | 凯特立斯（深圳）科技有限公司 | Three tooth aminophosphine ligands and its complex and its application in the asymmetric catalytic hydrogenation of ketone |
-
2018
- 2018-07-09 CN CN201810741762.5A patent/CN108864210A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103831133A (en) * | 2014-02-25 | 2014-06-04 | 中国人民解放军第四军医大学 | Bi-functional phosphine thiourea organic catalyst based on ferrocene skeleton as well as preparation method and application thereof |
| CN107722068A (en) * | 2017-11-09 | 2018-02-23 | 凯特立斯（深圳）科技有限公司 | Three tooth aminophosphine ligands and its complex and its application in the asymmetric catalytic hydrogenation of ketone |
Non-Patent Citations (2)
| Title |
|---|
| HAIWEN HU等: "Chiral bifunctional ferrocenylphosphine catalyzed highly enantioselective [3+2] cycloaddition reaction", 《ORG. BIOMOL. CHEM.》 * |
| YUAN-ZHAO MO等: "Asymmetric transfer hydrogenation of γ-aryl α,γ-dioxo-butyric acid esters", 《RSC ADV.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109078653A (en) * | 2018-10-08 | 2018-12-25 | 浙江工业大学上虞研究院有限公司 | Chiral ferrocene phosphoric acid catalyst and its application in asymmetric Friedel-Crafts reaction |
| CN114853820A (en) * | 2022-05-13 | 2022-08-05 | 江苏医药职业学院 | Ferrocene and camphorsulfonic acid composite derivative, preparation method thereof and application thereof in catalyzing asymmetric P-S reaction |
| CN114853820B (en) * | 2022-05-13 | 2023-12-15 | 江苏医药职业学院 | Ferrocene and camphorsulfonic acid composite derivative, preparation method thereof and application thereof in catalyzing asymmetric P-S reaction |
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