CN111072460A - Preparation method of norbornene compound containing ether long chain - Google Patents
Preparation method of norbornene compound containing ether long chain Download PDFInfo
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- CN111072460A CN111072460A CN201911357571.XA CN201911357571A CN111072460A CN 111072460 A CN111072460 A CN 111072460A CN 201911357571 A CN201911357571 A CN 201911357571A CN 111072460 A CN111072460 A CN 111072460A
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- norbornene
- ether
- long chain
- based compounds
- methanol
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 60
- -1 norbornene compound Chemical class 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 20
- 238000010992 reflux Methods 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 12
- 238000009987 spinning Methods 0.000 claims abstract description 10
- 239000008367 deionised water Substances 0.000 claims abstract description 8
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 8
- 239000012074 organic phase Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000007530 organic bases Chemical class 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 239000011261 inert gas Substances 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000003208 petroleum Substances 0.000 claims description 7
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical group CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- LUMNWCHHXDUKFI-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethanol Chemical compound C1C2C(CO)CC1C=C2 LUMNWCHHXDUKFI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- HUTXVUPGARJNHM-UHFFFAOYSA-N 1-(2-chloroethoxy)ethanol Chemical group CC(O)OCCCl HUTXVUPGARJNHM-UHFFFAOYSA-N 0.000 claims description 3
- IGHHPVIMEQGKNE-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]methanol Chemical compound C1C2C=CC1C(CO)C2CO IGHHPVIMEQGKNE-UHFFFAOYSA-N 0.000 claims description 3
- 150000002848 norbornenes Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000012973 diazabicyclooctane Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 231100000956 nontoxicity Toxicity 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NSTVHFOHEYKXRQ-UHFFFAOYSA-N 4-bicyclo[2.2.1]hept-2-enylmethanol Chemical compound C1CC2C=CC1(CO)C2 NSTVHFOHEYKXRQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- 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
- C07C45/64—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 introduction of functional groups containing oxygen only in singly bound form
-
- 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
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/40—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing six carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of norbornene compounds containing ether long chains, which comprises the following steps: adding organic base into a three-mouth bottle, replacing air in the three-mouth bottle with inert gas, adding a solvent, and slowly adding a norbornene methanol compound for reflux; then slowly adding halogenated alkane or halogenated alkane derivative into the three-necked bottle for reactionThe reaction solution is washed by deionized water for layering, the organic phase is spun off low-boiling substances and anhydrous MgSO is used4Drying overnight; purifying the product by column chromatography, removing low-boiling-point substances by spinning, adding CaH into the product2Refluxing, and distilling under reduced pressure to obtain norbornene compounds containing ether long chain. The method can obtain the target product with higher yield, has the characteristics of low cost, simple process, less pollution, safety, no toxicity and the like, and is very expected to carry out large-scale industrial production.
Description
Technical Field
The invention relates to a preparation method of a norbornene compound containing an ether long chain, belonging to the technical field of organic synthesis.
Background
The cycloolefin copolymer is an amorphous thermoplastic material, has the characteristics of low density, low hygroscopicity, low birefringence, high transparency, high strength, acid and alkali resistance and the like, and is widely applied to the production of high-density optical disks, optical lenses, barrier films and medical appliances.
The flexible group (long-chain alkane) is introduced into the norbornene chain, so that not only can excellent performances of the norbornene, such as good mechanical property and thermal property, low gas permeability, corrosion resistance and the like, be maintained, but also the solubility, toughness and processability of the norbornene compound containing the functional group can be greatly improved.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide the preparation method of the norbornene compound containing the ether long chain, which has the advantages of low cost, high yield, simple process, and safe and nontoxic long-chain halogenated alkane.
According to the technical scheme provided by the invention, the preparation method of the norbornene compound containing the ether long chain is characterized by comprising the following steps of:
a. adding an organic base into a three-mouth bottle, replacing air in the three-mouth bottle with inert gas, adding a solvent, heating the system in the three-mouth bottle to 40-120 ℃, slowly adding a norbornene methanol compound, and refluxing for 1-3 hours at 40-120 ℃, wherein the molar ratio of the organic base to the norbornene methanol compound is 4: 1-10: 1;
b. slowly adding halogenated alkane or halogenated alkane derivatives into the three-necked bottle, and reacting for 12-36 hours at 40-120 ℃, wherein the molar ratio of the norbornene methanol compound to the halogenated butane is 1: 1-3: 1;
c. the reaction solution is washed by deionized water for layering, the organic phase is removed by spinning low-boiling-point substances and anhydrous MgSO is used4Drying overnight;
d. purifying the product by column chromatography, removing low-boiling-point substances by spinning, adding CaH into the product2Refluxing, and distilling under reduced pressure of 0.1MPa at 20-50 deg.C to obtain norbornene compounds containing long ether chain.
Preferably, the organic base is Et3One or more of N, DBU, DABCO or DMDEA.
Preferably, the solvent is one or two of THF or DCM.
Preferably, the chemical structural formula of the norbornene methanol compound is shown as the formula (I):
in formula I, R is selected from hydroxyl, hydroxyl-substituted derivative group, aldehyde-substituted derivative group or hydrogen.
Preferably, the norbornene methanol-based compound is 5-norbornene-2, 3-dimethanol, 5-norbornene-2-methanol-3-carbaldehyde, 5-norbornene-2-methanol, or 5-norbornene-2-methanol-3-carbonitrile.
Preferably, the halogenated alkane is n-butyl chloride.
Preferably, the halogenated alkane derivative is 2-chloroethoxyethanol.
Preferably, the norbornene compound containing the ether long chain has a chemical structural formula shown in formula (II):
in the formula II, R is selected from hydroxyl, hydroxyl substituted derivative group, aldehyde substituted derivative group or hydrogen, and R' is an aliphatic chain or an ether chain;
preferably, an eluent formed by mixing petroleum ether and ethyl acetate according to the volume ratio of (4-6): 1 is used for column chromatography.
The raw materials, alkali and solvent used in the invention are all industrial commodities, are simple and easily available, have wide sources and low price, have very stable performance and do not need special storage conditions. The method can obtain the target product with higher yield, has the characteristics of low cost, simple process, less pollution, safety, no toxicity and the like, and is very expected to carry out large-scale industrial production.
Detailed Description
The present invention will be further described with reference to the following specific examples.
The invention will be further illustrated with reference to the following specific examples. These examples are intended to illustrate the invention and are not intended to limit the scope of the invention. Simple replacement or improvement of the present invention by those skilled in the art is within the technical scheme of the present invention.
Example 1
A method for preparing an ether long-chain norbornene compound by introducing long-chain alkyl to a norbornene alcohol compound comprises the following steps:
a. 20.2g Et was added to a 250mL three-necked flask3N, replacing three times with nitrogen, adding 100mL of anhydrous THF, heating the internal system of the three-necked flask to 60 ℃, then dropwise adding 6.0mL of 5-norbornene-2, 3-dimethanol (recorded as 1a) and maintaining the temperature of 60 ℃ for refluxing for 2 hours;
b. then, 11mL of n-butyl chloride (2) is dropwise added, the dropwise adding time is controlled to be about l h, and finally the reaction is carried out for 24 hours at 60 ℃;
c. the reaction solution is washed by deionized water for layering, the organic phase is removed by spinning low-boiling-point substances and anhydrous MgSO is used4Drying overnight;
d. purifying the product by column (eluent is prepared: the volume ratio of petroleum ether to ethyl acetate is 4:1), removing low-boiling-point substances by rotation, and adding CaH2After refluxing, the target product (3 a) was obtained by distilling off at 35 ℃ and 0.08MPa with a yield of 82 wt%.
The reaction process of the above step is shown as the following formula (1):
the nuclear magnetic data for product 3a is as follows:
1H NMR(400MHz,CDCl3)δ6.00(s,2H),3.58(d,J＝10.0Hz,2H),3.32(t,J＝9.2,2H).3.24-3.08(m,4H),2.76(s,2H),2.49(d,J＝6.0Hz,2H),1.96-1.43(m,10H),1.12-0.87(m,6H).13C NMR(101MHz,CDCl3)δ134.8,72.57,70.14,63.30,49.9,46.52,31.78,19.07,14.12。
example 2
A method for preparing an ether long-chain norbornene compound by introducing long-chain alkyl to a norbornene alcohol compound comprises the following steps:
a. 20.2g Et was added to a 250mL three-necked flask3Replacing the solution with nitrogen for three times, adding 100mL of anhydrous THF, heating the system in a three-necked bottle to 70 ℃, dropwise adding 6.0mL of 5-norbornene-2-methanol-3-formaldehyde (marked as 1b) and maintaining the temperature of 70 ℃ for refluxing for 2 hours;
b. dropwise adding 11mL of n-butyl chloride (2), controlling the dropwise adding time to be about l h, and finally reacting for 24h at 70 ℃;
c. the reaction solution is washed by deionized water for layering, the organic phase is removed by spinning low-boiling-point substances and anhydrous MgSO is used4Drying overnight;
d. purifying the product by column (eluent is prepared: the volume ratio of petroleum ether to ethyl acetate is 4:1), removing low-boiling-point substances by rotation, and adding CaH2After refluxing, the target product (3 b) was obtained by distilling off at 30 ℃ and 0.09MPa with a yield of 79 wt%.
The reaction process of the above step is shown as the following formula (2):
example 3
A method for preparing an ether long-chain norbornene compound by introducing long-chain alkyl to a norbornene alcohol compound comprises the following steps:
a. 20.2g Et was added to a 250mL three-necked flask3N, replacing three times with nitrogen, adding 100mL of anhydrous DCM, heating the internal system of the three-necked flask to 60 ℃, then dropwise adding 4.0mL of 5-norbornene-2-methanol (recorded as 1c) and maintaining the reflux at 60 ℃ for 2 h;
b. dropwise adding 11mL of n-butyl chloride (recorded as 2), controlling the dropwise adding time to be about l h, and finally reacting for 24h at 60 ℃;
c. the reaction solution is washed by deionized water for layering, the organic phase is removed by spinning low-boiling-point substances and anhydrous MgSO is used4Drying overnight;
d. purifying the product by column (eluent is prepared: the volume ratio of petroleum ether to ethyl acetate is 6: 1), removing low-boiling-point substances by rotation, and adding CaH2After refluxing, the target product (3 c) was obtained by distillation at 35 ℃ under 0.07MPa, with a yield of 71 wt%.
The reaction process of the above step is shown as the following formula (3):
example 4
A method for preparing an ether long-chain norbornene compound by introducing long-chain alkyl to a norbornene alcohol compound comprises the following steps:
a. 20.2g Et was added to a 250mL three-necked flask3N, replacing three times with nitrogen, adding 100mL of anhydrous THF, heating the internal system of the three-necked flask to 80 ℃, then dropwise adding 5-norbornene-2-methanol-3-carbonitrile (recorded as 1d) to 5.0mL, and maintaining the temperature of 80 ℃ for refluxing for 2 h;
b. dropwise adding 11mL of n-butyl chloride (recorded as 2), controlling the dropwise adding time to be about l h, and finally reacting for 24h at 80 ℃;
c. the reaction solution is washed by deionized water for layering, the organic phase is removed by spinning low-boiling-point substances and anhydrous MgSO is used4Drying overnight;
d. purifying the product by column (eluent is prepared: the volume ratio of petroleum ether to ethyl acetate is 4:1), removing low-boiling-point substances by rotation, and adding CaH2Refluxing, distilling off at 35 deg.C and 0.07Mpa to obtain target product (3 d), with yield of 79wt％。
The reaction process of the above step is shown as the following formula (4):
example 5
A method for preparing an ether long-chain norbornene compound by introducing long-chain alkyl to a norbornene alcohol compound comprises the following steps:
a. 20.2g Et was added to a 250mL three-necked flask3N, replacing three times with nitrogen, adding 100mL of anhydrous DCM, heating the internal system of the three-necked flask to 60 ℃, then dropwise adding 4.0mL of 5-norbornene-2-methanol (recorded as 1c) and maintaining the temperature of 60 ℃ for refluxing for 2 h;
b. then dropwise adding 11mL of 2-chloroethoxy ethanol (recorded as 2), controlling the dropwise adding time to be about l h, and finally reacting for 24h at 60 ℃;
c. the reaction solution is washed by deionized water for layering, the organic phase is removed by spinning low-boiling-point substances and anhydrous MgSO is used4Drying overnight;
d. purifying the product by column (eluent is prepared: the volume ratio of petroleum ether to ethyl acetate is 4:1), removing low-boiling-point substances by rotation, and adding CaH2After refluxing, the target product (3 e) was obtained by distilling off under reduced pressure at 45 ℃ and 0.07MPa, with a yield of 76 wt%.
The reaction process of the above step is shown as the following formula (5):
Claims (9)
1. a preparation method of norbornene compounds containing ether long chains is characterized by comprising the following steps:
a. adding an organic base into a three-mouth bottle, replacing air in the three-mouth bottle with inert gas, adding a solvent, heating the system in the three-mouth bottle to 40-120 ℃, slowly adding a norbornene methanol compound, and refluxing for 1-3 hours at 40-120 ℃, wherein the molar ratio of the organic base to the norbornene methanol compound is 4: 1-10: 1;
b. slowly adding halogenated alkane or halogenated alkane derivatives into the three-necked bottle, and reacting for 12-36 hours at 40-120 ℃, wherein the molar ratio of the norbornene methanol compound to the halogenated butane is 1: 1-3: 1;
c. the reaction solution is washed by deionized water for layering, the organic phase is removed by spinning low-boiling-point substances and anhydrous MgSO is used4Drying overnight;
d. purifying the product by column chromatography, removing low-boiling-point substances by spinning, adding CaH into the product2Refluxing, and distilling under reduced pressure of 0.1MPa at 20-50 deg.C to obtain norbornene compounds containing long ether chain.
2. The method for producing norbornene-based compounds having an ether long chain according to claim 1, wherein: the organic base is Et3One or more of N, DBU, DABCO or DMDEA.
3. The method for producing norbornene-based compounds having an ether long chain according to claim 1, wherein: the solvent is one or two of THF or DCM.
4. The method for producing norbornene-based compounds having an ether long chain according to claim 1, wherein: the chemical structural formula of the norbornene methanol compound is shown as the formula (I):
in formula I, R is selected from hydroxyl, hydroxyl-substituted derivative group, aldehyde-substituted derivative group or hydrogen.
5. The method for producing norbornene-based compounds having an ether long chain according to claim 4, wherein: the norbornene methanol compound is 5-norbornene-2, 3-dimethanol, 5-norbornene-2-methanol-3-formaldehyde, 5-norbornene-2-methanol or 5-norbornene-2-methanol-3-carbonitrile.
6. The method for producing norbornene-based compounds having an ether long chain according to claim 1, wherein: the halogenated alkane is n-butyl chloride.
7. The method for producing norbornene-based compounds having an ether long chain according to claim 1, wherein: the halogenated alkane derivative is 2-chloroethoxy ethanol.
8. The method for producing norbornene-based compounds having an ether long chain according to claim 1, wherein: the norbornene compound containing the ether long chain has a chemical structural formula shown in a formula (II):
in formula II, R is selected from hydroxyl, hydroxyl substituted derivative group, aldehyde substituted derivative group or hydrogen, and R' is an aliphatic chain or an ether chain.
9. The method for producing norbornene-based compounds having an ether long chain according to claim 1, wherein: and during column chromatography purification, an eluant formed by mixing petroleum ether and ethyl acetate according to the volume ratio of (4-6): 1 is used.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866497A (en) * | 2017-01-22 | 2017-06-20 | 中北大学 | A kind of norborneol vinyl compound and its preparation method and application |
| CN109704923A (en) * | 2018-06-28 | 2019-05-03 | 江苏新瑞药业有限公司 | A kind of preparation method of 5- norbornene -2- methanol |
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- 2019-12-25 CN CN201911357571.XA patent/CN111072460A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866497A (en) * | 2017-01-22 | 2017-06-20 | 中北大学 | A kind of norborneol vinyl compound and its preparation method and application |
| CN109704923A (en) * | 2018-06-28 | 2019-05-03 | 江苏新瑞药业有限公司 | A kind of preparation method of 5- norbornene -2- methanol |
Non-Patent Citations (1)
| Title |
|---|
| TOM G. DRIVER等: "Diastereoselective Silacyclopropanations of Functionalized Chiral Alkenes", 《J. AM. CHEM. SOC.》 * |
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