CN104844429B - A kind of method of gold catalysis pinacol rearrangement - Google Patents

A kind of method of gold catalysis pinacol rearrangement Download PDF

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CN104844429B
CN104844429B CN201510175333.2A CN201510175333A CN104844429B CN 104844429 B CN104844429 B CN 104844429B CN 201510175333 A CN201510175333 A CN 201510175333A CN 104844429 B CN104844429 B CN 104844429B
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pinacol
minutes
gold catalysis
gold
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CN104844429A (en
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刘永祥
程卯生
石慧
王晓宇
杜川
金盛飞
刘洋
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Shenyang Pharmaceutical University
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    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/52—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule

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Abstract

The invention provides a kind of method of gold catalysis pinacol rearrangement, reaction expression is as follows, wherein R1,R2,R3,R4,Can be common alkyl, cycloalkyl, aromatic rings.The required Au catalyst of reaction is Ph3PAuCl, Ph3PAuNTf2, HAuCl4, NaAuCl4, Ph3PAuOTf, Ph3PAuSbF6, IPrAuCl, nanometer gold.The required medium of reaction is：Toluene, sym-trimethylbenzene., 1,2 dichloroethanes, oxolane, acetonitrile, acetone.The microwave reactor that is embodied as of reaction heats, the inventive method, simple to operate, applied range, reaction green.

Description

A kind of method of gold catalysis pinacol rearrangement
Technical field
The present invention relates to one kind is in the presence of Au catalyst, pinacol be dehydrated under microwave mediation formation corresponding aldehyde or The method of ketone.
Background technology
Pinacol rearrangement is that 1,2- glycol issues raw intramolecular rearrangement dehydration in acid catalysiss and generates carbonyl compound The reaction of (aldehydes or ketones), product pinacoline is a kind of important organic chemical industry's intermediate, is widely used in pesticide medical science dyestuff etc. The synthesis of multiple fine chemicals.(J.Org.Chem.2000,65 (22), 7438-7446.) generally, pinacol rearrangement is In inorganic acid such as H2SO4Carry out under catalysis, not only selectivity is not high, and serious to equipment corrosion, to environment. Therefore, the development trend that the strong mineral acid of corrosivity is this field is replaced with solid acid.Solid acid common at present has：
(1) samarium diodide, (S.J.Jong et.al.J.Organomet.Chem., 1999,590,42-45.), the method It is published in 1999, flowed back with substrate in oxolane using samarium diodide and so that substrate is reset.But, the method Substrate applicability is not high, and from reaction equation, the substrate of the method is only limitted to symmetrical vicinal diamines, and must in substituted radical Must there is the such structure of ferrocene, therefore this solid acid does not have good range of application.
(2) ferric chloride (A.B.Shinde et.al.Synth.Commun., 2004,34,309-314.), first will FeCl3On the immobilized K10 to montmorillonite, the montmorillonite K10 then being modified with this Fe (III), as catalyst, is heated back in toluene Stream.The method has only done five substrates, and catalyst prepare that some are time-consuming, selectivity is very bad.Wherein Ph and Ar moves The ratio moved is close to 1:1, separate highly difficult, there is no good using value.
(3) high molecular polymer (C.Pavlik et.al.Synlett., 2011,15,2191-2194.).This reaction Major defect is that the response time is oversize, needs overnight.And polymer catalyst still needs to prepare.In substrate applicability side Face, different substrates also will add different acid to carry out further activated catalyst, for example：Glacial acetic acid, concentrated sulphuric acid etc..Yield is not yet It is very high, 70% about.Sometimes even up to 160 DEG C of reaction temperature.Application is not high.
(4)ZnCl2/SiO2(D.J.Upadhyaya et.al.Applied Catalysis A:General.,2008, 340,42-51.).It is a kind of method of utilization carrier solid-carried catalyst, by ZnCl2Grind SiO2On.The early stage of this method is accurate Standby ratio is relatively time-consuming, needs SiO23 hours more than are dried under 120 DEG C of high temperature.And the time is how about a hour, The longest reaches more than six hours, inefficient.
In sum it is known that catalysis pinacol rearrangement solid acid in, or reaction required for temperature higher, or reaction Selectivity is not high, or catalyst early stage prepare more complicated, or reaction time long.Therefore find a kind of selectivity high And the gentle catalyst of reaction condition is very urgent.Au catalyst water stability preferably, is utilized to be catalyzed pinacol rearrangement Reaction is a kind of green, environmental protection, has no the brand-new method of document report, has good application prospect.
Content of the invention
The present invention relates to a kind of new method of pinacol rearrangement, that is, using gold as catalyst, under microwave mediation, adjacent Glycol is directly rearranged into ketone or aldehyde, and reaction expression is：
Wherein R1,R2,R3,R4, can be hydrogen, C1-C10 alkyl, C3-C8 cycloalkyl, C1-C10 alkoxyl, or C6- C10 aromatic radical, preferably hydrogen, C1-C4 alkyl, C3-C8 cycloalkyl, C1-C4 alkoxyl or C6-C10 aromatic radical, more preferably：Hydrogen, Phenyl, ethyoxyl, cyclopropyl.C6-C10 aromatic radical can be phenyl, thienyl, furyl, the aromatic such as pyridine, or The C6-C10 aromatic radical that C1-C4 alkyl, halogen, C1-C4 alkoxyl, nitro, cyano group replace.
WhereinIt can be following structure：
The catalyst being used is Au catalyst, is preferably wherein Ph3PAuNTf2, but be not limited to：Ph3PAuCl、 Ph3PAuNTf2、HAuCl4、NaAuCl4、Ph3PAuOTf、Ph3PAuSbF6, IPrAuCl, nanometer gold.
The consumption of described catalyst is the 0.5%-1% of the amount of material of reactant.Selected solvent is preferably 1,2- dichloroethanes, but be not limited to：Toluene, sym-trimethylbenzene., oxolane, acetonitrile, dioxane, acetone.Preparation process is：
(1) feed
Reaction substrate is added in reaction microwave tube, adds the solvent of 1-10 times that consumption is reactant to be situated between as reaction Matter.Reaction medium is 1,2- dichloroethanes, but is not limited to：Solvent-free, toluene, sym-trimethylbenzene., oxolane, acetonitrile, acetone A kind of.It is subsequently adding the 0.5%-5% Au catalyst of the amount of material that consumption is reactant.Preferably 1%.The gold catalysis being used Agent, is preferably wherein Ph3PAuNTf2, but be not limited to：Ph3PAuCl、Ph3PAuNTf2、HAuCl4、NaAuCl4、Ph3PAuOTf、 Ph3PAuSbF6, IPrAuCl, nanometer gold.The addition sequence of reactant, reaction medium and Au catalyst can arbitrarily exchange.
(2) react
Make temperature of charge in microwave reactor at 50 DEG C 150 DEG C, stirring reaction 3 minutes 60 minutes, with thin layer Chromatograph detects course of reaction.The developing solvent of thin layer chromatography be petroleum ether, ethyl acetate, normal hexane, methanol, chloroform, dichloromethane, Acetone, the mixed liquor of oxolane, water or both or three therein.Preferably：Petrol ether/ethyl acetate (v:100/1～5/ 1) or n-hexane/ethyl acetate (v:100/1～5/1) system.
(3) reactant liquor post processing
Reactant liquor Rotary Evaporators after cooling are steamed reaction medium, straight to reactant mixture with silica gel or aluminium oxide Tap into the purification of row column chromatography for separation and obtain target product, the system of developing solvent is：Petroleum ether, ethyl acetate, normal hexane, methanol, Chloroform, dichloromethane, acetone, the mixed liquor of oxolane, water or both or three therein.Preferably：Petroleum ether/acetic acid second Ester (v:100/1～5/1) or n-hexane/ethyl acetate (v:100/1～5/1) system.
The invention has the advantages that, chemically from the perspective of, reaction condition is gentle, and the response time is short, simple to operate, from work From the perspective of industry and environment, post processing is simple, environmental protection.
Specific embodiment
Contact following example, be better understood with advantages of the present invention and preparation process, these embodiments be intended to illustrate and It is not to limit the scope of the present invention.
Embodiment 1：
Substrate 1 (1mmol, 27.4mg) is added to be simultaneously introduced Ph in the microwave tube of 10mL3PAuCl (0.01mmol, 0.5mg), add 0.2mL 1,2 dichloroethanes as reaction dissolvent, reactant mixture microwave reactor be heated to 80 DEG C, Stirring reaction 20 minutes, after the completion of reaction, is separated with the method for rapid column chromatography and obtains target product I, yield 93%.
Reaction equation is：
The spectral data of product II is：ESI-MS(m/z):273.25[M+H]+；1H NMR(600MHz,DMSO)δ9.87 (d, J=1.8Hz, 1H), 7.20 7.13 (m, 4H), 6.97 6.91 (m, 4H), 4.99 (d, J=1.6Hz, 1H), 3.73 (s, 6H).
Embodiment 2：
Replace substrate 1 with substrate 2, other obtain target compound II, yield 96% with embodiment 1.
Reaction equation is：
The spectral data of product II is：ESI-MS(m/z):377.15[M+H]+；1H NMR(600MHz,DMSO)δ9.94 (d, J=2.1Hz, 1H), 6.66 (s, 4H), 4.90 (d, J=2.0Hz, 1H), 3.76 (s, 12H), 3.64 (s, 6H).
Embodiment 3：
Replace substrate 1 with substrate 3, other obtain target compound III, yield 67% with embodiment 1.
Reaction equation is：
The spectral data of product III is：ESI-MS(m/z):233.07[M+H]+；1H NMR(600MHz,CDCl3)δ9.90 (d, J=2.1Hz, 1H), 7.20 7.14 (m, 4H), 7.10 7.05 (m, 4H), 4.87 (d, J=1.4Hz, 1H).
Embodiment 4：
Replace substrate 1 with substrate 4, other obtain target compound IV, yield 57% with embodiment 1.
Reaction equation is：
The spectral data of product IV is：ESI-MS(m/z):265.01[M+H]+；1H NMR(600MHz,DMSO)δ9.79 (d, J=5.7Hz, 1H), 7.36 (d, J=8.6Hz, 2H), 7.32 (t, J=8.0Hz, 4H), 7.14 (d, J=8.5Hz, 2H), 6.97 (d, J=5.8Hz, 1H).
Embodiment 5：
Substrate 5 (1mmol, 24.2mg) is added to be simultaneously introduced Ph in the microwave tube of 10mL3PAuNTf2(0.01mmol, 0.7mg), add 0.2mL 1,2 dichloroethanes as reaction dissolvent, reactant mixture microwave reactor be heated to 90 DEG C, Stirring reaction 10 minutes, after the completion of reaction, separates to obtain target compound V, yield 87% with the method for rapid column chromatography.
Reaction equation is：
The spectral data of product V is：ESI-MS(m/z):243.13[M+H]+；1H NMR(600MHz,CDCl3)δ7.35 (dd, J=10.4,4.7Hz, 4H), 7.31 7.26 (m, 2H), 7.23 7.19 (m, 4H), 2.12 (s, 3H), 1.89 (s, 3H).
Embodiment 6：
Replace substrate 5 with substrate 6, other obtain target compound VI, yield 89% with embodiment 5.
Reaction equation is：
The spectral data of product VI is：ESI-MS(m/z):271.16[M+H]+；1H NMR(600MHz,CDCl3)δ7.14 (d, J=8.1Hz, 4H), 7.08 (d, J=8.2Hz, 4H), 2.35 (s, 6H), 2.10 (s, 3H), 1.83 (s, 3H).
Embodiment 7：
Replace substrate 5 with substrate 7, other obtain target compound VII, yield 96% with embodiment 5.
Reaction equation is：
The spectral data of product VII is：ESI-MS(m/z):303.15[M+H]+；1H NMR(600MHz,CDCl3)δ 7.16 6.97 (m, 4H), 6.86 (d, J=8.9Hz, 4H), 3.81 (s, 6H), 2.09 (s, 3H), 1.82 (s, 3H).
Embodiment 8：
Replace substrate 5 with substrate 8, other obtain target compound VIII, yield 76% with embodiment 5.
Reaction equation is：
The spectral data of product VII I is：ESI-MS(m/z):279.11[M+H]+；1H NMR(600MHz,CDCl3)δ 7.16–7.11(m,4H),7.06–7.00(m,4H),2.11(s,3H),1.86(s,3H).
Embodiment 9：
Substrate 9 (1mmol, 18.2mg) is added to be simultaneously introduced Ph in the microwave tube of 10mL3PAuNTf2(0.01mmol, 0.7mg), add 0.2mL 1,2 dichloroethanes as reaction dissolvent, reactant mixture microwave reactor be heated to 100 DEG C, Stirring reaction 10 minutes, after the completion of reaction, separates to obtain target compound IX, yield 81% with the method for rapid column chromatography.
Reaction equation is：
The spectral data of product IX is：ESI-MS(m/z):163.11[M+H]+；1H NMR(600MHz,CDCl3)δ7.39– 7.33(m,2H),7.29–7.25(m,3H),1.93(s,3H),1.49(s,6H).
Embodiment 10：
Replace substrate 9 with substrate 10, other obtain target compound X, yield 71% with embodiment 9.
The spectral data of product X is：ESI-MS(m/z):177.12[M+H]+；1H NMR(600MHz,CDCl3)δ7.15 (s,4H),2.34(s,3H),1.92(s,3H),1.46(s,6H).
Embodiment 11：
Substrate 11 (1mmol, 19.4mg) is added to be simultaneously introduced Ph in the microwave tube of 10mL3PAuNTf2(0.05mmol, 3.5mg), add 0.2mL 1,2 dichloroethanes as reaction dissolvent, reactant mixture microwave reactor be heated to 100 DEG C, Stirring reaction 10 minutes, after the completion of reaction, separates to obtain target compound IX, yield 70% with the method for rapid column chromatography
The spectral data of product X is：ESI-MS(m/z):177.12[M+H]+；1H NMR(600MHz,CDCl3)δ7.15 (s,4H),2.34(s,3H),1.92(s,3H),1.46(s,6H).
Embodiment 12：
Substrate 11 (1mmol, 19.4mg) is added to be simultaneously introduced Ph in the microwave tube of 10mL3PAuNTf2(0.005mmol, 0.35mg), add 0.2mL 1,2 dichloroethanes as reaction dissolvent, reactant mixture microwave reactor is heated to 100 DEG C, stirring reaction 10 minutes, after the completion of reaction, separate to obtain target compound IX, yield 49% with the method for rapid column chromatography
The spectral data of product X is：ESI-MS(m/z):177.12[M+H]+；1H NMR(600MHz,CDCl3)δ7.15 (s,4H),2.34(s,3H),1.92(s,3H),1.46(s,6H).

Claims (24)

1. a kind of gold catalysis pinacol rearrangement method it is characterised in that：With gold as catalyst, under microwave mediation, frequently Which alcohol is reset generates corresponding aldehydes or ketones, and reaction expression is：
Wherein R1,R2,R3,R4, independently selected from hydrogen, C1-C10 alkyl, C3-C8 cycloalkyl, C1-C10 alkoxyl, or C6-C10 Aromatic radical, described C6-C10 aromatic radical is phenyl, thienyl, furyl, pyridine, or C1-C4 alkyl, halogen, C1-C4 alcoxyl The C6-C10 aromatic radical that base, nitro, cyano group replace；Described Au catalyst, selected from Ph3PAuCl、Ph3PAuNTf2、HAuCl4、 NaAuCl4、Ph3PAuOTf、Ph3PAuSbF6, IPrAuCl, nanometer gold.
2. as claimed in claim 1 a kind of gold catalysis pinacol rearrangement method it is characterised in that：R1,R2,R3,R4, it is Hydrogen, C1-C4 alkyl, C3-C8 cycloalkyl, C1-C4 alkoxyl or C6-C10 aromatic radical.
3. as claimed in claim 1 gold catalysis pinacol rearrangement method it is characterised in that：R1,R2,R3,R4, be hydrogen, Phenyl, ethyoxyl, cyclopropyl.
4. as described in claim 1-3 any one a kind of gold catalysis pinacol rearrangement method it is characterised in that：Instead Should medium or reaction medium be no oxolane, 1,2- dichloroethanes, toluene, sym-trimethylbenzene., methanol, acetonitrile, N, N- dimethyl Methanamide or dimethyl sulfoxide.
5. as described in claim 1-3 any one a kind of gold catalysis pinacol rearrangement method it is characterised in that：Instead Medium is answered to be 1,2- dichloroethanes.
6. as described in claim 1-3 any one a kind of gold catalysis pinacol rearrangement method it is characterised in that：Urge The consumption of agent is the 0.5%-5% of the amount of material of reactant.
7. as claimed in claim 4 a kind of gold catalysis pinacol rearrangement method it is characterised in that：The consumption of catalyst 0.5%-5% for the amount of the material of reactant.
8. as claimed in claim 5 a kind of gold catalysis pinacol rearrangement method it is characterised in that：The consumption of catalyst 0.5%-5% for the amount of the material of reactant.
9. the method for a kind of gold catalysis pinacol rearrangement as described in claim 1-3,7-8 any one, its feature exists In：Described reaction microwave reactor is heated at 50 DEG C -150 DEG C, stirring reaction 3 minutes 60 minutes.
10. as claimed in claim 4 a kind of gold catalysis pinacol rearrangement method it is characterised in that：Described reaction It is heated at 50 DEG C -150 DEG C with microwave reactor, stirring reaction 3 minutes 60 minutes.
11. as claimed in claim 5 a kind of gold catalysis pinacol rearrangement method it is characterised in that：Described reaction It is heated at 50 DEG C -150 DEG C with microwave reactor, stirring reaction 3 minutes 60 minutes.
12. as claimed in claim 6 a kind of gold catalysis pinacol rearrangement method it is characterised in that：Described reaction It is heated at 50 DEG C -150 DEG C with microwave reactor, stirring reaction 3 minutes 60 minutes.
A kind of method of the 13. gold catalysis pinacol rearrangements as any one of claim 1-3,7-8,10-12, It is characterized in that：Its preparation process is as follows：
(1) pinacol is added in reaction microwave tube, adds the solvent that consumption is 1-10 times of reactant as reaction medium；
(2) make temperature of charge in microwave reactor at 50 DEG C 150 DEG C, stirring reaction 3 minutes 60 minutes, with thin layer color Spectrum detects course of reaction, and the system of developing solvent is：Petroleum ether, ethyl acetate, normal hexane, methanol, chloroform, dichloromethane, acetone, The mixed liquor of oxolane, water or both or three therein.
14. right want as described in 4 a kind of gold catalysis pinacol rearrangement methods it is characterised in that：Its preparation process is such as Under：
(1) pinacol is added in reaction microwave tube, adds the solvent that consumption is 1-10 times of reactant as reaction medium；
(2) make temperature of charge in microwave reactor at 50 DEG C 150 DEG C, stirring reaction 3 minutes 60 minutes, with thin layer color Spectrum detects course of reaction, and the system of developing solvent is：Petroleum ether, ethyl acetate, normal hexane, methanol, chloroform, dichloromethane, acetone, The mixed liquor of oxolane, water or both or three therein.
15. right want as described in 5 a kind of gold catalysis pinacol rearrangement methods it is characterised in that：Its preparation process is such as Under：
(1) pinacol is added in reaction microwave tube, adds the solvent that consumption is 1-10 times of reactant as reaction medium；
(2) make temperature of charge in microwave reactor at 50 DEG C 150 DEG C, stirring reaction 3 minutes 60 minutes, with thin layer color Spectrum detects course of reaction, and the system of developing solvent is：Petroleum ether, ethyl acetate, normal hexane, methanol, chloroform, dichloromethane, acetone, The mixed liquor of oxolane, water or both or three therein.
16. right want as described in 6 a kind of gold catalysis pinacol rearrangement methods it is characterised in that：Its preparation process is such as Under：
(1) pinacol is added in reaction microwave tube, adds the solvent that consumption is 1-10 times of reactant as reaction medium；
(2) make temperature of charge in microwave reactor at 50 DEG C 150 DEG C, stirring reaction 3 minutes 60 minutes, with thin layer color Spectrum detects course of reaction, and the system of developing solvent is：Petroleum ether, ethyl acetate, normal hexane, methanol, chloroform, dichloromethane, acetone, The mixed liquor of oxolane, water or both or three therein.
17. right want as described in 9 a kind of gold catalysis pinacol rearrangement methods it is characterised in that：Its preparation process is such as Under：
(1) pinacol is added in reaction microwave tube, adds the solvent that consumption is 1-10 times of reactant as reaction medium；
(2) make temperature of charge in microwave reactor at 50 DEG C 150 DEG C, stirring reaction 3 minutes 60 minutes, with thin layer color Spectrum detects course of reaction, and the system of developing solvent is：Petroleum ether, ethyl acetate, normal hexane, methanol, chloroform, dichloromethane, acetone, The mixed liquor of oxolane, water or both or three therein.
18. as claimed in claim 13 a kind of gold catalysis pinacol rearrangement method it is characterised in that：By step (2) Steam reaction medium with Rotary Evaporators after obtaining reactant liquor cooling, with silica gel or aluminium oxide, post is directly carried out to reactant mixture Chromatography purifies.
A kind of method of the 19. gold catalysis pinacol rearrangements as any one of claim 14-17, its feature exists In：Step (2) is obtained steaming reaction medium with Rotary Evaporators after reactant liquor cooling, with silica gel or aluminium oxide to reaction mixing Thing directly carries out column chromatography for separation purification.
20. as claimed in claim 18 a kind of gold catalysis pinacol rearrangement method it is characterised in that：Chromatography launches The system of agent is：Petroleum ether, ethyl acetate, normal hexane, methanol, chloroform, dichloromethane, acetone, oxolane, water or wherein Both or three mixed liquor.
21. as claimed in claim 19 a kind of gold catalysis pinacol rearrangement method it is characterised in that：Chromatography launches The system of agent is：Petroleum ether, ethyl acetate, normal hexane, methanol, chloroform, dichloromethane, acetone, oxolane, water or wherein Both or three mixed liquor.
22. as claimed in claim 13 a kind of gold catalysis pinacol rearrangement method it is characterised in that：Described expansion Agent is petrol ether/ethyl acetate=100/1～5/1 or n-hexane/ethyl acetate=100/1～5/1.
A kind of method of the 23. gold catalysis pinacol rearrangements as described in claim 14-18 any one, its feature exists In：Described developing solvent is petrol ether/ethyl acetate=100/1～5/1 or n-hexane/ethyl acetate=100/1～5/1.
24. as claimed in claim 19 a kind of gold catalysis pinacol rearrangement method it is characterised in that：Described expansion Agent is petrol ether/ethyl acetate=100/1～5/1 or n-hexane/ethyl acetate=100/1～5/1.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4628120A (en) * 1983-10-19 1986-12-09 Toyo Stauffer Chemical Co., Ltd. Preparing method of optically active ketones
CN104039759A (en) * 2012-01-10 2014-09-10 科勒研究有限公司 Chiral Imidodiphosphates And Derivatives Thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57142938A (en) * 1981-02-27 1982-09-03 Sumitomo Chem Co Ltd Preparation of pinacolone

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4628120A (en) * 1983-10-19 1986-12-09 Toyo Stauffer Chemical Co., Ltd. Preparing method of optically active ketones
CN104039759A (en) * 2012-01-10 2014-09-10 科勒研究有限公司 Chiral Imidodiphosphates And Derivatives Thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
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Rapid and efficient protic ionic liquid-mediated pinacol rearrangements under microwave irradiation;L. C. Henderson et al.;《Green Chem.》;20110221;第13卷;813-816 *

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