CN114752634A - Preparation method of (R) 3-butyne-2-ol derivative - Google Patents
Preparation method of (R) 3-butyne-2-ol derivative Download PDFInfo
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- CN114752634A CN114752634A CN202210474173.1A CN202210474173A CN114752634A CN 114752634 A CN114752634 A CN 114752634A CN 202210474173 A CN202210474173 A CN 202210474173A CN 114752634 A CN114752634 A CN 114752634A
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- GKPOMITUDGXOSB-SCSAIBSYSA-N (2r)-but-3-yn-2-ol Chemical class C[C@@H](O)C#C GKPOMITUDGXOSB-SCSAIBSYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 16
- 102000004190 Enzymes Human genes 0.000 claims abstract description 13
- 108090000790 Enzymes Proteins 0.000 claims abstract description 13
- 108010031132 Alcohol Oxidoreductases Proteins 0.000 claims abstract description 9
- 102000005751 Alcohol Oxidoreductases Human genes 0.000 claims abstract description 9
- 238000010531 catalytic reduction reaction Methods 0.000 claims abstract 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000005515 coenzyme Substances 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- XRGPFNGLRSIPSA-UHFFFAOYSA-N butyn-2-one Chemical class CC(=O)C#C XRGPFNGLRSIPSA-UHFFFAOYSA-N 0.000 claims description 8
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000006555 catalytic reaction Methods 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 claims description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 4
- GKPOMITUDGXOSB-UHFFFAOYSA-N but-3-yn-2-ol Chemical class CC(O)C#C GKPOMITUDGXOSB-UHFFFAOYSA-N 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229940078552 o-xylene Drugs 0.000 claims description 2
- 239000008055 phosphate buffer solution Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical group C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229950006238 nadide Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- -1 compound (R) 3-butyn-2-ol derivative Chemical class 0.000 abstract description 6
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000006722 reduction reaction Methods 0.000 abstract 2
- 239000012074 organic phase Substances 0.000 description 6
- 239000008363 phosphate buffer Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical class OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing a compound (R) 3-butyn-2-ol derivative shown in a formula (II) by a reduction reaction of a compound 3-butyn-2-one derivative shown in the formula (I), wherein the reduction reaction is an enzyme catalytic reduction reaction, and the enzyme is selected from carbonyl reductase. The method can effectively prepare the target compound, has the advantages of simple operation, environmental protection, high yield, high selectivity, low cost and the like, and is suitable for industrial production.
Description
Technical Field
The invention relates to a preparation method of (R) 3-butyne-2-alcohol derivatives.
Background
The chiral propargyl alcohol derivative is an important intermediate for synthesizing natural products such as alkaloid, steroid, sesquiterpene and the like,
the specific structural formula is as follows:
the synthesis of this intermediate has been reported in the current patent (CN102408313A), which discloses the following route:
racemic 3-butyne-2-alcohol is taken as a raw material, firstly reacts with phthalic anhydride, and then R-phenylethylamine is subjected to salt formation and resolution to finally obtain (R) 3-butyne-2-alcohol, but in the route, after the compound is subjected to salt formation, the compound needs to be crystallized and purified for multiple times to obtain a final product. There are also relevant literature reports (R) methods for the preparation of 3-butyn-2-ol derivatives (Thomas Schubert; Werner Hummel; Maria-Regina Kula; Michael Muller. organic Synthesis of Both elastomers of vacuum polymeric Alcohols by Use of Two oxygen products EurJOC.2001(22), 4181-4187), but these processes have one or more of the following problems: 1) a great amount of high-concentration acid-containing wastewater and waste liquid can be generated in the splitting process; 2) the yield is low, the production period is long, and the production cost is increased; 3) the reaction system is too large, the productivity is low, and the method is not suitable for industrial scale-up production.
Disclosure of Invention
In view of the above problems, the present invention provides a process for producing a 3-butyn-2-one derivative represented by the formula (I) below as an (R) 3-butyn-2-ol derivative represented by the formula (II) below:
said R is1Selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and the like;
the reaction is an enzyme catalyzed reaction, the enzyme being selected from carbonyl reductases.
Further, the temperature of the enzyme-catalyzed reaction is 20-60 ℃, preferably 37-45 ℃;
the time of the enzyme catalysis reaction is 12-96 hours, preferably 18-48 hours.
Further, the enzyme-catalyzed reaction is carried out in an aqueous solvent system.
Further, the aqueous solvent is selected from mixed solvents consisting of phosphate and organic solvents.
Further, the organic solvent is selected from one or more of methyl tert-butyl ether, isopropyl ether, ethyl acetate, tetrahydrofuran, dichloromethane, toluene, o-xylene, m-xylene, p-xylene and acetone; preferably, the organic solvent is selected from one or more of methyl tert-butyl ether, isopropyl ether, acetone and toluene; most preferably, the organic solvent is selected from methyl tert-butyl ether.
Further, the mass ratio of the compound shown in the formula (I) to the enzyme is 100: 1-1: 1, preferably 30: 1-10: 1;
Furthermore, the mass ratio of the compound shown in the formula (I) to the coenzyme is 10000: 1-10: 1, preferably 1000: 1-100: 1.
Further, the phosphate solution is a phosphate buffer solution with a pH value of 7.2, and the volume ratio of the phosphate to the organic solvent in the mixed solvent is 100: 1-1: 1, preferably 10: 1-4: 1.
Further, the mass-to-volume ratio of the compound of formula (I) to the solvent is 1: 5-1: 20, preferably 1: 10-1: 15.
Test results prove that the method can effectively prepare the target compound and has the advantages of simple operation, environmental protection, high yield, high selectivity, low cost and the like.
Obviously, many modifications, substitutions, and variations are possible in light of the above teachings of the invention, without departing from the basic technical spirit of the invention, as defined by the following claims.
The present invention will be described in further detail with reference to the following examples. This should not be understood as limiting the scope of the above-described subject matter of the present invention to the following examples. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
Detailed Description
In the examples, the enzyme reagent is derived from Nippon wild enzyme preparation Co., Ltd, and the coenzyme is derived from Bangtai bioengineering (Shenzhen) Co., Ltd.
Example 1
(R) preparation of 3-butyn-2-ol:
in phosphate buffer (250mL), 3-butyn-2-one (50g), carbonyl reductase K1(2.5g), coenzyme (NADPH,0.05g), methyl tert-butyl ether (62.5mL), isopropanol (10mL), the reaction was stirred at 37 ℃, after 26 hours, the reaction was terminated, methyl tert-butyl ether (250mL) was added and extracted 2 times, the organic phases were combined, dried and spun to give 45g of an oil (compound of formula (ii)), ee 99.2%, and yield 90%.
Example 2
To a phosphate buffer (500mL) was added 3-butyn-2-one (50g), carbonyl reductase K2(2.5g), coenzyme (NADH, 0.5g), methyl tert-butyl ether (50mL), isopropanol (10mL), the reaction was stirred at 45 ℃ and terminated after 18 hours, methyl tert-butyl ether (250mL) was added and extracted 2 times, the organic phases were combined, dried and spun to give 42g of an oil (compound of formula (II)), ee 99.6%, and yield 84%.
Example 3
To a phosphate buffer (500mL) was added 3-butyn-2-one (50g), carbonyl reductase K2(1.6g), coenzyme (NADH, 0.05g), methyl tert-butyl ether (50mL), isopropanol (10mL), the reaction was stirred at 45 ℃ and stopped after 38 hours, methyl tert-butyl ether (250mL) was added and extracted 2 times, the organic phases were combined, dried and spun to give 44g of an oil (compound of formula (II)) with ee 99.6% and yield 88%.
Example 4
After stirring in phosphate buffer (750mL), 3-butyn-2-one (50g), carbonyl reductase K3(5g), coenzyme (0.02g), isopropyl ether (75mL), and isopropanol (10mL) at room temperature for 38 hours, the reaction was terminated, methyl tert-butyl ether (250mL) was added and extracted 2 times, the organic phases were combined, dried, and spun to give 41g of an oil (compound of formula (ii)), ee 98.5%, and yield 82%.
Example 5
To a phosphate buffer (500mL) was added 3-butyn-2-one (50g), carbonyl reductase K4(1.6g), coenzyme (NADPH, 0.1g), acetone (50mL), isopropanol (10mL), stirred at room temperature, quenched after 48 hours, extracted 2 times with methyl tert-butyl ether (250mL), and the organic phases were combined, dried and spun to give 43.5g of an oil (compound of formula (II)), ee 97.5%, and yield 87%.
Example 6
(R) preparation of 1-butyn-3-ol:
1-butyn-3-one (50g), carbonyl reductase K2(2.5g), coenzyme (NADH, 0.5g), methyl t-butyl ether (50mL), isopropyl alcohol (10mL) were added to phosphate buffer (500mL), the reaction was stirred at 45 ℃ and stopped after 24 hours, methyl t-butyl ether (250mL) was added and extracted 2 times, the organic phases were combined, dried and spun to obtain 45.3g of an oil (compound of formula (IIb)), ee 99.4%, yield 90.6%
In conclusion, the high-purity alkynol intermediate can be effectively prepared, has the advantages of simplicity in operation, environmental friendliness, high yield, high selectivity, low cost and the like, and can be applied to industrial production.
Claims (8)
1. A process for producing a 3-butyn-2-ol derivative of the compound (R) of the formula (II) from a 3-butyn-2-one derivative of the compound of the formula (I), characterized by comprising the steps of:
1) taking a compound shown in a formula (I) as a raw material, taking isopropanol as a hydrogen source in a water-containing solvent system, and carrying out enzyme catalytic reduction to obtain (R) 3-butyn-2-ol derivatives;
wherein, R is1Selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and the like;
the enzyme is selected from carbonyl reductases;
the coenzyme is selected from reduced nicotinamide adenine dinucleotide phosphate (abbreviated as NADPH) or nicotinamide adenine dinucleotide (abbreviated as NADH).
2. The method of claim 1, wherein: the temperature of the enzyme catalytic reaction is 20-60 ℃;
the time of the enzyme catalysis reaction is 12-96 hours.
3. The method according to claim 1 or 2, characterized in that: the enzyme-catalyzed reaction is carried out in an aqueous solvent system.
4. The method of claim 3, wherein: the aqueous solvent is selected from a mixed solvent consisting of phosphate and an organic solvent.
5. The method according to claim 3, wherein the organic solvent is one or more selected from methyl tert-butyl ether, isopropyl ether, ethyl acetate, tetrahydrofuran, dichloromethane, toluene, o-xylene, m-xylene, p-xylene, and acetone.
6. The method of claim 1, wherein: the mass ratio of the compound shown in the formula (I) to the enzyme is 100: 1-1: 1; the mass ratio of the compound shown in the formula (I) to the coenzyme is 10000: 1-10: 1.
7. The method of claim 4, wherein: the phosphate solution is a phosphate buffer solution with the pH value of 7.2, and the volume ratio of phosphate to the organic solvent in the mixed solvent is 100: 1-1: 1.
8. The method according to any one of claims 3 or 4, wherein: the mass volume ratio of the compound shown in the formula (I) to the solvent is 1: 5-1: 20.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2362070A1 (en) * | 1999-02-16 | 2000-08-24 | Masaru Mitsuda | Substituted acetylpyridine derivatives and process for the preparation of intermediates for optically active .beta.3 agonist by the use of the same |
| WO2007042444A1 (en) * | 2005-10-10 | 2007-04-19 | Basf Se | New esterases and their use for processes for kinetic resolution of butinolesters |
| CN102946898A (en) * | 2010-06-19 | 2013-02-27 | 天野酶株式会社 | Agent for reducing acetaldehyde in oral cavity |
-
2022
- 2022-04-29 CN CN202210474173.1A patent/CN114752634A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2362070A1 (en) * | 1999-02-16 | 2000-08-24 | Masaru Mitsuda | Substituted acetylpyridine derivatives and process for the preparation of intermediates for optically active .beta.3 agonist by the use of the same |
| WO2007042444A1 (en) * | 2005-10-10 | 2007-04-19 | Basf Se | New esterases and their use for processes for kinetic resolution of butinolesters |
| CN101253262A (en) * | 2005-10-10 | 2008-08-27 | 巴斯夫欧洲公司 | New esterases and their use for processes for kinetic resolution of butinolesters |
| CN102946898A (en) * | 2010-06-19 | 2013-02-27 | 天野酶株式会社 | Agent for reducing acetaldehyde in oral cavity |
Non-Patent Citations (1)
| Title |
|---|
| 胡锐;张承平;裴志胜;: "光动不对称加氢制备高光学纯度(S)-4-三甲基硅基-3-丁炔-2-醇的研究", 化学学报, no. 07, 15 July 2013 (2013-07-15), pages 1064 - 1070 * |
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