CN107827931B - Using '-biphenyl diphenol as bidentate phosphite ester ligand of structural unit and preparation method thereof - Google Patents
Using '-biphenyl diphenol as bidentate phosphite ester ligand of structural unit and preparation method thereof Download PDFInfo
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- CN107827931B CN107827931B CN201711225293.3A CN201711225293A CN107827931B CN 107827931 B CN107827931 B CN 107827931B CN 201711225293 A CN201711225293 A CN 201711225293A CN 107827931 B CN107827931 B CN 107827931B
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- 239000003446 ligand Substances 0.000 title claims abstract description 34
- 150000008301 phosphite esters Chemical class 0.000 title claims abstract description 19
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000004305 biphenyl Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 18
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 claims 2
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims 1
- RLMOMHNXIWBGTF-UHFFFAOYSA-N diaminophosphinoamine Chemical compound NP(N)N RLMOMHNXIWBGTF-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 238000006555 catalytic reaction Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000010189 synthetic method Methods 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 6
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000004679 31P NMR spectroscopy Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 238000007037 hydroformylation reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DISPOJHKKXSCLS-UHFFFAOYSA-N n-diaminophosphorylmethanamine Chemical compound CNP(N)(N)=O DISPOJHKKXSCLS-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000005086 pumping Methods 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of using '-biphenyl diphenol as bidentate phosphite ester ligand of structural unit and preparation method thereof, and the structural formula of the ligand is as follows:
Description
Technical field
The invention belongs to technical field of organic synthesis, and in particular to using '-biphenyl diphenol as the bidentate phosphite ester of structural unit
The preparation method of ligand.
Background technique
Ligand often has a decisive role in the reaction of organic catalysis, for many reactions, is only added
Catalyst reaction can not occur.Reaction allows to be also required to exacting terms, such as: high temperature, high pressure etc..Research hair
Existing, after ligand is added in the reaction, reaction can occur in a mild condition.In addition to this, using for ligand can also make separately
Some examples that can not be reacted successfully realize (Pure Appl Chem., 2000, 18(1): 1233 ~1246)。
Scientists have synthesized a plurality of types of phosphite ester ligands using '-biphenyl diphenol as structural unit.1995,
Van Leeuwen seminar reports a kind of novel chiral bidentate phosphite ligand, and the ligand is applied to styrene
Asymmetric hydroformylation reaction in (Chem. Soc. Dalton. Trans., 1995, 409).1996, Van
Leeuwen et al. design has synthesized one kind using '-biphenyl diphenol as the phosphite ester ligand of structural unit, and it is pungent in 1- to investigate it
In alkene and styrene hydroformylation reaction application (Organometallics, 1996,15:835~847).2008, sharp object
The Xiao Jianliang of Pu university teaches seminar[19]An article about acrylamide hydroformylation reaction is reported, they are using connection
Benzenediol be structural unit monodentate phosphite ligands (Tetrahedron: Letters, 2008, 49: 3516~
3519)。
Although the report of various bidentate phosphite ester ligands is more, using '-biphenyl diphenol as the bidentate phosphorous of structural unit
The report research of ester ligand is less so far, therefore has certain reality and theory significance to the synthesis of such compound.
Summary of the invention
It is an object of the present invention to provide a kind of using '-biphenyl diphenol as the compound of the bidentate phosphite ester ligand of structural unit and
Preparation method, this method is easy, easy, and obtained ligand is expected to be used widely in organic catalysis field.
To achieve the above object, the invention adopts the following technical scheme:
Bidentate phosphite ester ligand of the invention is connection knot with trans cvclohexvl glycol using '-biphenyl diphenol as structural unit
Structure, ligand structure formula are as follows:
。
The preparation method of the ligand, steps are as follows:
(1) under anhydrous and oxygen-free inert gas shielding, in organic solvent by the dissolution of 2,2 '-dihydroxybiphenyls, six are added dropwise
Methyl phosphoric triamide (HMPT) after being added dropwise, under 20-150 °C, reacts 1-10 hour；
(2) stop heating, after reaction system is cooled to room temperature, trans cvclohexvl glycol, reaction temperature are added under nitrogen protection
Degree is 25-140 °C, and the reaction time is 2-8 hour, and concentrated liquid removes most of solvent, then is recrystallized to give white solid
Bidentate phosphite ester ligand；Preparation route is as follows:
。
The molar ratio of 2,2 '-dihydroxybiphenyls and hexamethylphosphoramide (HMPT) are 1:1-4 in the step (1).
The molar ratio of 2,2 '-dihydroxybiphenyls and trans cvclohexvl glycol is 1-3:1 in the step (2).
The molar ratio of 2,2 '-dihydroxybiphenyls and organic solvent is 1:30-90 in the step (1), wherein organic solvent
For benzene, toluene, ethylbenzene, chlorobenzene, dimethylbenzene, methylene chloride, tetrahydrofuran, chloroform, pyridine, DMF or DMSO.
Beneficial effects of the present invention: synthetic method of the invention is easy to operate, raw materials used cheap and easy to get.The ligand has
Stable structure, to water, air is insensitive the advantages that.There is extensive potential using value in terms of many organic catalytic reactions,
Therefore, the present invention is expected to be applied in organic synthesis field.
Specific embodiment
Combined with specific embodiments below, the present invention will be further described.It should be understood that following embodiment is merely to illustrate this
The person skilled in the art of the range of invention and is not intended to limit the present invention, the field can make one according to the content of foregoing invention
A little nonessential modifications and adaptations.
Embodiment 1
The present embodiment using '-biphenyl diphenol as the structural formula of the bidentate phosphite ester ligand of structural unit are as follows:
；
The present embodiment using '-biphenyl diphenol as the bidentate phosphite ester ligand of structural unit the preparation method is as follows:
(1) to drying, 2,2'- dihydroxybiphenyl (558mg, 3.0mmol) is added in clean 50mL three-necked flask, with oil
Pumping vacuum simultaneously replaces N2Three times, in N2Protection is lower to be added the dry chlorobenzene of 12mL, HPMT (1.74mL, 12.00mmol), at 20 °C
Under the conditions of stir 10h；
(2) stop heating, be cooled to room temperature to reaction solution in N2The lower addition trans cvclohexvl glycol of protection (0.10mL,
1.0mmol), reaction temperature is 25 °C, and the reaction time is 8 hours, and filtering, filtrate is spin-dried for obtaining product, be obtained using recrystallization method
789mg white solid, yield 95%. Mp: 67-69 °C;1H NMR (600 MHz, CDCl3, SiMe4): δ 7.45-
7.13 (m, 16H), 4.27 (m, 2H), 2.09 (d, J = 13.8 Hz, 2H), 1.68-1.66 (m, 2H),
1.53 (t, J = 10.2 Hz, 2H), 1.25 (t, J = 9.3 Hz, 2H); 13C NMR (150 MHz, CDCl3,
SiMe4): δ 148.75, 148.71, 148.49, 148,45, 130.28, 130.02, 128.79, 128.76,
128.07, 127.98, 124.03, 123.86, 121.26, 121.18, 30.99, 21.88; 31P NMR (243
MHz, CDCl3, HPO4) δ 146.38. HRMS (ESI+) calcd for C63H92O6P2 [M+H] + : 545.1290,
found 545.1290.
Embodiment 2
The present embodiment using '-biphenyl diphenol as the bidentate phosphite ester ligand of structural unit the preparation method is as follows:
(1) it to drying, is added 2,2'- dihydroxybiphenyl (558mg, 3.0mmol), uses in clean 100mL three-necked flask
Oil pump vacuumizes and replaces N2Three times, in N2Protection is lower to be added 35mL dry toluene, HPMT (0.22mL, 1.5mmol), at 150 °C
Under the conditions of stir 1h；
(2) stop heating, be cooled to room temperature to reaction solution in N2The lower addition trans cvclohexvl glycol of protection (0.15mL,
1.5mmol), reaction temperature is 140 °C, and the reaction time is 2 hours, and filtering, filtrate is spin-dried for obtaining product, using recrystallization method
Obtain 789mg white solid, yield 95%. Mp: 67-69 °C;1H NMR (600 MHz, CDCl3, SiMe4): δ 7.45-
7.13 (m, 16H), 4.27 (m, 2H), 2.09 (d, J = 13.8 Hz, 2H), 1.68-1.66 (m, 2H),
1.53 (t, J = 10.2 Hz, 2H), 1.25 (t, J = 9.3 Hz, 2H); 13C NMR (150 MHz, CDCl3,
SiMe4): δ 148.75, 148.71, 148.49, 148,45, 130.28, 130.02, 128.79, 128.76,
128.07, 127.98, 124.03, 123.86, 121.26, 121.18, 30.99, 21.88; 31P NMR (243
MHz, CDCl3, HPO4) δ 146.38. HRMS (ESI+) calcd for C63H92O6P2 [M+H] + : 545.1290,
found 545.1290.
Embodiment 3
The present embodiment using '-biphenyl diphenol as the bidentate phosphite ester ligand of structural unit the preparation method is as follows:
(1) it to drying, is added 2,2'- dihydroxybiphenyl (558mg, 3.0mmol), uses in clean 100mL three-necked flask
Oil pump vacuumizes and replaces N2Three times, in N2The dry dimethylbenzene of the lower addition 30mL of protection, HPMT (1.06mL, 7.32mmol),
3 h are stirred under the conditions of 100 °C；
(2) stop heating, be cooled to room temperature to reaction solution in N2The lower addition trans cvclohexvl glycol of protection (0.30mL,
3.0mmol), reaction temperature is 90 °C, and the reaction time is 3 hours, and filtering, filtrate is spin-dried for obtaining product, using recrystallization method
Obtain 789mg white solid, yield 95%. Mp: 67-69 °C;1H NMR (600 MHz, CDCl3, SiMe4): δ 7.45-
7.13 (m, 16H), 4.27 (m, 2H), 2.09 (d, J = 13.8 Hz, 2H), 1.68-1.66 (m, 2H),
1.53 (t, J = 10.2 Hz, 2H), 1.25 (t, J = 9.3 Hz, 2H); 13C NMR (150 MHz, CDCl3,
SiMe4): δ 148.75, 148.71, 148.49, 148,45, 130.28, 130.02, 128.79, 128.76,
128.07, 127.98, 124.03, 123.86, 121.26, 121.18, 30.99, 21.88; 31P NMR (243
MHz, CDCl3, HPO4) δ 146.38. HRMS (ESI+) calcd for C63H92O6P2 [M+H] + : 545.1290,
found 545.1290.
Basic principles and main features and advantages of the present invention of the invention have been shown and described above.The skill of the industry
Art personnel it should be appreciated that the present invention is not limited to the above embodiments, the above embodiments and description only describe
The principle of the present invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these
Changes and improvements all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and
Its equivalent thereof.
Claims (4)
1. a kind of using '-biphenyl diphenol as the preparation method of the bidentate phosphite ester ligand of structural unit, which is characterized in that step is such as
Under:
(1) under anhydrous and oxygen-free inert gas shielding, in organic solvent by the dissolution of 2,2 '-dihydroxybiphenyls, hexamethyl is added dropwise
Phosphorous acid triamide after being added dropwise, under 20-150 °C, reacts 1-10 hour；The hexamethyl phosphorous acid triamide
Molecular formula is [(CH3)2N]3P；
(2) stop heating, after reaction system is cooled to room temperature, trans cvclohexvl glycol is added under nitrogen protection, reaction temperature is
25-140 °C, the reaction time is 2-8 hour, and concentrated liquid removes most of solvent, then is recrystallized to give white solid bidentate
Phosphite ester ligand；The structural formula of the ligand are as follows:
。
2. it is according to claim 1 using '-biphenyl diphenol as the preparation method of the bidentate phosphite ester ligand of structural unit,
Be characterized in that: the molar ratio of 2,2 '-dihydroxybiphenyls and hexamethyl phosphorous acid triamide is 1:1-4 in the step (1).
3. it is according to claim 1 using '-biphenyl diphenol as the preparation method of the bidentate phosphite ester ligand of structural unit,
Be characterized in that: the molar ratio of 2,2 '-dihydroxybiphenyls and trans cvclohexvl glycol is 1-3:1 in the step (2).
4. it is according to claim 1 using '-biphenyl diphenol as the preparation method of the bidentate phosphite ester ligand of structural unit,
Be characterized in that: the molar ratio of 2,2 '-dihydroxybiphenyls and organic solvent is 1:30-90 in the step (1), wherein organic solvent
For benzene, toluene, ethylbenzene, chlorobenzene, dimethylbenzene, methylene chloride, tetrahydrofuran, chloroform, pyridine, DMF or DMSO.
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| CN108947754B (en) * | 2018-08-30 | 2021-02-26 | 郑州大学 | Use of bidentate phosphite ligands in C-F bond building reactions |
| CN111203276B (en) * | 2020-02-27 | 2022-11-18 | 郑州大学 | Application of chiral bidentate phosphite ligand, hydrosilation reaction catalyst and application thereof, and preparation method of chiral silane |
| CN111203277B (en) * | 2020-02-27 | 2022-11-18 | 郑州大学 | Application of chiral bidentate phosphite ligand, conia-Ene reaction catalyst and method for constructing chiral quaternary carbon center |
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|---|---|---|---|---|
| CN1768070A (en) * | 2003-03-28 | 2006-05-03 | 陶氏环球技术公司 | Asymmetric catalysts prepared from optically active bisphosphites bridged by achiral diols |
| WO2016087264A1 (en) * | 2014-12-04 | 2016-06-09 | Evonik Degussa Gmbh | Monophosphites which contain a naphthol |
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2017
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|---|---|---|---|---|
| CN1768070A (en) * | 2003-03-28 | 2006-05-03 | 陶氏环球技术公司 | Asymmetric catalysts prepared from optically active bisphosphites bridged by achiral diols |
| WO2016087264A1 (en) * | 2014-12-04 | 2016-06-09 | Evonik Degussa Gmbh | Monophosphites which contain a naphthol |
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| Title |
|---|
| Chiral diphosphites derived from (1R ,2 R)- trans -1,2-cyclohexanediol: a new class of ligands for asymmetric hydrogenations;Zeng-bo Pang et al;《Tetrahedron:Asymmetry》;20151231;第26卷;第1389–1393页 * |
| Design of a new class of chiral quinoline–phosphine ligands. Synthesis and application in asymmetric catalysis;Guillaume Delapierre et al;《Tetrahedron: Asymmetry》;20011231;第1345-1352页 * |
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