DE10100971A1 - Verfahren zur Herstellung enantiomerenangereicherter beta-Aminosäure - Google Patents
Verfahren zur Herstellung enantiomerenangereicherter beta-AminosäureInfo
- Publication number
- DE10100971A1 DE10100971A1 DE10100971A DE10100971A DE10100971A1 DE 10100971 A1 DE10100971 A1 DE 10100971A1 DE 10100971 A DE10100971 A DE 10100971A DE 10100971 A DE10100971 A DE 10100971A DE 10100971 A1 DE10100971 A1 DE 10100971A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- cycloalkyl
- beta
- amino
- aryl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 150000001576 beta-amino acids Chemical class 0.000 title claims abstract description 16
- 239000002798 polar solvent Substances 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 title claims abstract description 12
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 238000003786 synthesis reaction Methods 0.000 title claims description 7
- 230000000975 bioactive effect Effects 0.000 title claims description 4
- 239000000126 substance Substances 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 title description 8
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical class N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 34
- 238000005984 hydrogenation reaction Methods 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 13
- 239000003446 ligand Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 5
- 238000009901 transfer hydrogenation reaction Methods 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 239000011593 sulfur Substances 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- -1 β-amino acid ester Chemical class 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 6
- 239000010948 rhodium Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000003708 ampul Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- YTLYLLTVENPWFT-UHFFFAOYSA-N 3-aminoprop-2-enoic acid Chemical class NC=CC(O)=O YTLYLLTVENPWFT-UHFFFAOYSA-N 0.000 description 2
- 150000001371 alpha-amino acids Chemical class 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000012041 precatalyst Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- LYXHWHHENVLYCN-QMDOQEJBSA-N (1z,5z)-cycloocta-1,5-diene;rhodium;tetrafluoroborate Chemical compound [Rh].F[B-](F)(F)F.C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 LYXHWHHENVLYCN-QMDOQEJBSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ULBXWWGWDPVHAO-UHFFFAOYSA-N Chlorbufam Chemical compound C#CC(C)OC(=O)NC1=CC=CC(Cl)=C1 ULBXWWGWDPVHAO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 125000005610 enamide group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- ZXKCZLZDERMMQB-ARJAWSKDSA-N methyl (Z)-3-acetamidoprop-2-enoate Chemical compound COC(=O)\C=C/NC(C)=O ZXKCZLZDERMMQB-ARJAWSKDSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- 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
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10100971A DE10100971A1 (de) | 2001-01-11 | 2001-01-11 | Verfahren zur Herstellung enantiomerenangereicherter beta-Aminosäure |
| DE2001504095 DE50104095D1 (de) | 2001-01-11 | 2001-12-07 | Verfahren zur Herstellung enantiomerenangereicherter Beta-Aminosäure |
| EP01129076A EP1225166B1 (de) | 2001-01-11 | 2001-12-07 | Verfahren zur Herstellung enantiomerenangereicherter Beta-Aminosäure |
| AT01129076T ATE279388T1 (de) | 2001-01-11 | 2001-12-07 | Verfahren zur herstellung enantiomerenangereicherter beta-aminosäure |
| JP2002002691A JP4301757B2 (ja) | 2001-01-11 | 2002-01-09 | エナンチオマー濃縮されたＮ−アシル化されたβ−アミノ酸の製造方法並びに保護基分離によるβ−アミノ酸の製造方法及びその使用 |
| US10/042,256 US6492544B2 (en) | 2001-01-11 | 2002-01-11 | Process for synthesis of enantiomerically enriched β-amino acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10100971A DE10100971A1 (de) | 2001-01-11 | 2001-01-11 | Verfahren zur Herstellung enantiomerenangereicherter beta-Aminosäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10100971A1 true DE10100971A1 (de) | 2002-07-18 |
Family
ID=7670234
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10100971A Withdrawn DE10100971A1 (de) | 2001-01-11 | 2001-01-11 | Verfahren zur Herstellung enantiomerenangereicherter beta-Aminosäure |
| DE2001504095 Expired - Lifetime DE50104095D1 (de) | 2001-01-11 | 2001-12-07 | Verfahren zur Herstellung enantiomerenangereicherter Beta-Aminosäure |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2001504095 Expired - Lifetime DE50104095D1 (de) | 2001-01-11 | 2001-12-07 | Verfahren zur Herstellung enantiomerenangereicherter Beta-Aminosäure |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6492544B2 (enExample) |
| EP (1) | EP1225166B1 (enExample) |
| JP (1) | JP4301757B2 (enExample) |
| AT (1) | ATE279388T1 (enExample) |
| DE (2) | DE10100971A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005037649A1 (de) * | 2005-08-05 | 2007-02-08 | Leibniz-Institut Für Katalyse E.V. An Der Universität Rostock | Homogene katalytische Hydrierung |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7007861B2 (en) | 2000-06-08 | 2006-03-07 | S.C. Johnson & Son, Inc. | Methods and personal protection devices for repelling insects |
| BR0116160A (pt) * | 2000-12-13 | 2003-10-14 | Warner Lambert Co | Ligandos bisfosfolano p-quirais e seus complexos com metais de transição |
| JP4226847B2 (ja) * | 2001-07-24 | 2009-02-18 | 高砂香料工業株式会社 | ホスフィン−ホスホラン化合物と遷移金属とを含有する遷移金属錯体の存在下、α，β−不飽和アミド誘導体から光学活性アミド類を製造する方法。 |
| GB0120167D0 (en) * | 2001-08-17 | 2001-10-10 | Chirotech Technology Ltd | Asymmetric hydrogenation |
| EP1451133B1 (en) * | 2001-11-09 | 2017-10-25 | The Penn State Research Foundation | P-chiral phospholanes and phosphocyclic compounds and their use in asymmetric catalytic reactions |
| US7169953B2 (en) * | 2001-11-09 | 2007-01-30 | The Penn State Research Foundation | P-chiral phospholanes and phosphocyclic compounds and their use in asymmetric catalytic reactions |
| JP2005529868A (ja) * | 2002-04-04 | 2005-10-06 | デグサ アクチエンゲゼルシャフト | 二座配位子としてのビスホスフィン |
| US7084089B2 (en) * | 2002-07-31 | 2006-08-01 | Shell Oil Company | Process for the carbonylation of ethylenically unsaturated compounds, bidentate diphosphine composition used in this process and a process for preparation of this bidentate diphosphine composition |
| US6806391B2 (en) | 2002-07-31 | 2004-10-19 | Shell Oil Company | Process for the carbonylation of ethylenically unsaturated compounds and bidentate diphosphine composition used in this process |
| AR043515A1 (es) * | 2003-03-19 | 2005-08-03 | Merck & Co Inc | Procedimiento para preparar derivados quirales beta aminoacidos mediante hidrogenacion asimetrica |
| TW200602293A (en) * | 2004-04-05 | 2006-01-16 | Merck & Co Inc | Process for the preparation of enantiomerically enriched beta amino acid derivatives |
| US7013601B2 (en) * | 2004-07-22 | 2006-03-21 | Coastal Planters, Llc | Plant container with hanger |
| US7618410B2 (en) * | 2004-10-05 | 2009-11-17 | Cardia Access, Inc. | Devices and methods for access through a tissue wall |
| DE102005014055A1 (de) * | 2005-03-23 | 2006-09-28 | Degussa Ag | Unsymmetrisch substituierte Phospholankatalysatoren |
| EP2070903A1 (en) | 2007-12-12 | 2009-06-17 | Laboratorios del Dr. Esteve S.A. | Microwave-assisted ring opening reaction |
| EP2070904A1 (en) | 2007-12-12 | 2009-06-17 | Laboratorios Del. Dr. Esteve, S.A. | Rhodium-phosphorus complexes and their use in ring opening reactions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999059721A1 (en) * | 1998-05-18 | 1999-11-25 | The Penn State Research Foundation | Catalytic asymmetric hydrogenation, hydroformylation, and hydrovinylation via transition metal catalysts with phosphines and phosphites |
| EP1127061B1 (en) * | 1998-11-05 | 2003-03-05 | Chirotech Technology Limited | Chiral ligands for asymmetric catalysis |
-
2001
- 2001-01-11 DE DE10100971A patent/DE10100971A1/de not_active Withdrawn
- 2001-12-07 AT AT01129076T patent/ATE279388T1/de not_active IP Right Cessation
- 2001-12-07 DE DE2001504095 patent/DE50104095D1/de not_active Expired - Lifetime
- 2001-12-07 EP EP01129076A patent/EP1225166B1/de not_active Expired - Lifetime
-
2002
- 2002-01-09 JP JP2002002691A patent/JP4301757B2/ja not_active Expired - Fee Related
- 2002-01-11 US US10/042,256 patent/US6492544B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005037649A1 (de) * | 2005-08-05 | 2007-02-08 | Leibniz-Institut Für Katalyse E.V. An Der Universität Rostock | Homogene katalytische Hydrierung |
Also Published As
| Publication number | Publication date |
|---|---|
| US6492544B2 (en) | 2002-12-10 |
| EP1225166A1 (de) | 2002-07-24 |
| US20020128509A1 (en) | 2002-09-12 |
| EP1225166B1 (de) | 2004-10-13 |
| JP4301757B2 (ja) | 2009-07-22 |
| ATE279388T1 (de) | 2004-10-15 |
| DE50104095D1 (de) | 2004-11-18 |
| JP2002265425A (ja) | 2002-09-18 |
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