CS208483B2 - Method of asymetric hydrogenation - Google Patents

Method of asymetric hydrogenation Download PDF

Info

Publication number: CS208483B2
Authority: CS; Czechoslovakia
Prior art keywords: catalyst; hydrogenation; acid; reaction; substrate
Prior art date: 1977-10-17

Application number

CS786724A

Other languages

Czech (cs)

English (en)

Inventor

Marcello Mazzei

Mario Riocci

Walter Marconi

Original Assignee

Snam Progetti

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-10-17

Filing date

1978-10-16

Publication date

1981-09-15

1978-10-16 Application filed by Snam Progetti filed Critical Snam Progetti

1981-09-15 Publication of CS208483B2 publication Critical patent/CS208483B2/cs

Links

238000000034 method Methods 0.000 title claims description 9
238000005984 hydrogenation reaction Methods 0.000 title abstract description 10
239000003054 catalyst Substances 0.000 claims abstract description 23
239000010948 rhodium Substances 0.000 claims abstract description 12
229910052703 rhodium Inorganic materials 0.000 claims abstract description 7
239000000758 substrate Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
238000009876 asymmetric hydrogenation reaction Methods 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
-1 acetamino cinnamic acid Chemical compound 0.000 claims description 5
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 3
229930016911 cinnamic acid Natural products 0.000 claims description 3
235000013985 cinnamic acid Nutrition 0.000 claims description 3
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 3
UFDFFEMHDKXMBG-UHFFFAOYSA-N 2-acetamidoprop-2-enoic acid Chemical compound CC(=O)NC(=C)C(O)=O UFDFFEMHDKXMBG-UHFFFAOYSA-N 0.000 claims 1
229910052723 transition metal Inorganic materials 0.000 abstract description 5
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract description 4
150000003624 transition metals Chemical class 0.000 abstract description 4
150000001875 compounds Chemical class 0.000 abstract description 3
239000000440 bentonite Substances 0.000 abstract description 2
229910000278 bentonite Inorganic materials 0.000 abstract description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract description 2
125000002091 cationic group Chemical group 0.000 abstract description 2
KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 abstract description 2
229910000271 hectorite Inorganic materials 0.000 abstract description 2
229910052500 inorganic mineral Inorganic materials 0.000 abstract description 2
239000011707 mineral Substances 0.000 abstract description 2
239000002253 acid Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000002815 homogeneous catalyst Substances 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000002734 clay mineral Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
239000000047 product Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000002002 slurry Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241001154506 Vatica papuana Species 0.000 description 1
MCRWZBYTLVCCJJ-DKALBXGISA-N [(1s,3r)-3-[[(3s,4s)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[(1s,4s)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)[C@@]1(C[C@@H](CC1)N[C@@H]1[C@@H](COCC1)OC)C(C)C)[H])N2C1=CC(C(F)(F)F)=NC=N1 MCRWZBYTLVCCJJ-DKALBXGISA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000011982 enantioselective catalyst Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052621 halloysite Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
201000004792 malaria Diseases 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
150000003283 rhodium Chemical class 0.000 description 1
LJCXEFWMCQUXTD-UHFFFAOYSA-N rhodium dihydride Chemical compound [RhH2] LJCXEFWMCQUXTD-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910021647 smectite Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
- B01J31/1855—Triamide derivatives thereof
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1865—Phosphonites (RP(OR)2), their isomeric phosphinates (R2(RO)P=O) and RO-substitution derivatives thereof
- B01J31/187—Amide derivatives thereof
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
- B01J31/188—Amide derivatives thereof
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Inorganic Chemistry (AREA)
Materials Engineering (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS786724A 1977-10-17 1978-10-16 Method of asymetric hydrogenation CS208483B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT28666/77A IT1087963B (it)	1977-10-17	1977-10-17	Idrogenazione asimmetrica di olefine prochirali mediante complessi di metalli di transazione immobilizzati in minerali argillosi.

Publications (1)

Publication Number	Publication Date
CS208483B2 true CS208483B2 (en)	1981-09-15

Family

ID=11223981

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS786724A CS208483B2 (en)	1977-10-17	1978-10-16	Method of asymetric hydrogenation

Country Status (20)

Country	Link
JP (1)	JPS5466615A (da)
AU (1)	AU520574B2 (da)
BE (1)	BE871320A (da)
CA (1)	CA1148564A (da)
CH (1)	CH636589A5 (da)
CS (1)	CS208483B2 (da)
DD (1)	DD139251A5 (da)
DE (1)	DE2845216C2 (da)
DK (1)	DK461478A (da)
FR (1)	FR2405911A1 (da)
GB (1)	GB2006770B (da)
HU (1)	HU181953B (da)
IL (1)	IL55733A (da)
IT (1)	IT1087963B (da)
LU (1)	LU80370A1 (da)
NL (1)	NL7810236A (da)
NO (1)	NO148778C (da)
SE (1)	SE435923B (da)
YU (1)	YU237578A (da)
ZA (1)	ZA785486B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU190864B (en) *	1983-12-08	1986-11-28	Alkaloida Vegyeszeti Gyar	Process for production of phenil-alanin derivatives
GB8519008D0 (en) *	1985-07-27	1985-09-04	British Petroleum Co Plc	Chemical process

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4008281A (en) *	1973-12-03	1977-02-15	Monsanto Company	Asymmetric catalysis
CA1109074A (en) *	1976-04-26	1981-09-15	Mario Fiorini	Asymmetrical hydrogenation and related means for this purpose

1977
- 1977-10-17 IT IT28666/77A patent/IT1087963B/it active
1978
- 1978-09-25 CA CA000311978A patent/CA1148564A/en not_active Expired
- 1978-09-27 ZA ZA00785486A patent/ZA785486B/xx unknown
- 1978-09-27 AU AU40251/78A patent/AU520574B2/en not_active Expired
- 1978-10-09 JP JP12370578A patent/JPS5466615A/ja active Pending
- 1978-10-10 YU YU02375/78A patent/YU237578A/xx unknown
- 1978-10-11 GB GB7840114A patent/GB2006770B/en not_active Expired
- 1978-10-11 NL NL7810236A patent/NL7810236A/xx not_active Application Discontinuation
- 1978-10-13 IL IL55733A patent/IL55733A/xx unknown
- 1978-10-16 DD DD78208480A patent/DD139251A5/xx unknown
- 1978-10-16 CS CS786724A patent/CS208483B2/cs unknown
- 1978-10-16 SE SE7810776A patent/SE435923B/sv unknown
- 1978-10-16 CH CH1070078A patent/CH636589A5/it not_active IP Right Cessation
- 1978-10-16 DK DK461478A patent/DK461478A/da not_active Application Discontinuation
- 1978-10-16 HU HU78SA3141A patent/HU181953B/hu unknown
- 1978-10-16 NO NO783492A patent/NO148778C/no unknown
- 1978-10-16 LU LU80370A patent/LU80370A1/xx unknown
- 1978-10-16 FR FR7829446A patent/FR2405911A1/fr active Granted
- 1978-10-17 DE DE2845216A patent/DE2845216C2/de not_active Expired
- 1978-10-17 BE BE191166A patent/BE871320A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU4025178A (en)	1980-04-03
DE2845216A1 (de)	1979-04-19
DK461478A (da)	1979-04-18
IL55733A (en)	1981-11-30
NO148778C (no)	1983-12-14
JPS5466615A (en)	1979-05-29
DE2845216C2 (de)	1984-05-10
BE871320A (fr)	1979-04-17
IT1087963B (it)	1985-06-04
GB2006770A (en)	1979-05-10
NL7810236A (nl)	1979-04-19
FR2405911A1 (fr)	1979-05-11
GB2006770B (en)	1982-03-17
CH636589A5 (it)	1983-06-15
CA1148564A (en)	1983-06-21
YU237578A (en)	1983-01-21
IL55733A0 (en)	1978-12-17
SE435923B (sv)	1984-10-29
AU520574B2 (en)	1982-02-11
LU80370A1 (fr)	1979-03-19
ZA785486B (en)	1979-09-26
SE7810776L (sv)	1979-04-18
NO783492L (no)	1979-04-18
NO148778B (no)	1983-09-05
HU181953B (en)	1983-11-28
DD139251A5 (de)	1979-12-19
FR2405911B1 (da)	1981-03-20

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