JP2008504261A5 - - Google Patents
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- Publication number
- JP2008504261A5 JP2008504261A5 JP2007518135A JP2007518135A JP2008504261A5 JP 2008504261 A5 JP2008504261 A5 JP 2008504261A5 JP 2007518135 A JP2007518135 A JP 2007518135A JP 2007518135 A JP2007518135 A JP 2007518135A JP 2008504261 A5 JP2008504261 A5 JP 2008504261A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- compound
- formula
- hydrogen
- 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- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- -1 1,2-benzenediyl Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 239000011593 sulfur Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 229910052703 rhodium Inorganic materials 0.000 claims description 8
- 239000010948 rhodium Substances 0.000 claims description 8
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000005610 enamide group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 0 CC(C([C@@](C(*)CCC1CC2C3)C3=CC12N)N(*)P(*)*)=* Chemical compound CC(C([C@@](C(*)CCC1CC2C3)C3=CC12N)N(*)P(*)*)=* 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- WXUAQHNMJWJLTG-GSVOUGTGSA-N (R)-methylsuccinic acid Chemical compound OC(=O)[C@H](C)CC(O)=O WXUAQHNMJWJLTG-GSVOUGTGSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- RWPWEJJOJRYOLQ-UHFFFAOYSA-K [Rh+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.C1CC=CCCC=C1.C1CC=CCCC=C1 Chemical compound [Rh+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.C1CC=CCCC=C1.C1CC=CCCC=C1 RWPWEJJOJRYOLQ-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005356 chiral GC Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/876,387 US6906212B1 (en) | 2004-06-25 | 2004-06-25 | Phosphine-phosphoramidite compounds |
| PCT/US2005/021373 WO2006012045A1 (en) | 2004-06-25 | 2005-06-16 | Phosphine-phosphoramidite compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008504261A JP2008504261A (ja) | 2008-02-14 |
| JP2008504261A5 true JP2008504261A5 (enExample) | 2008-08-07 |
Family
ID=34634715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007518135A Withdrawn JP2008504261A (ja) | 2004-06-25 | 2005-06-16 | ホスフィン−ホスホロアミダイト化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6906212B1 (enExample) |
| EP (1) | EP1758844B1 (enExample) |
| JP (1) | JP2008504261A (enExample) |
| AT (1) | ATE491678T1 (enExample) |
| DE (1) | DE602005025346D1 (enExample) |
| WO (1) | WO2006012045A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6906212B1 (en) * | 2004-06-25 | 2005-06-14 | Eastman Chemical Company | Phosphine-phosphoramidite compounds |
| US6906213B1 (en) * | 2004-06-25 | 2005-06-14 | Eastman Chemical Company | Preparation of aminophosphines |
| WO2007020221A2 (en) * | 2005-08-12 | 2007-02-22 | Solvias Ag | Amino-phosphinoalkyl-ferrocenes and their use as ligands in catalysts for asymmetric reactions |
| CN100467479C (zh) * | 2005-10-20 | 2009-03-11 | 中国科学院大连化学物理研究所 | 一种膦-亚磷酰胺酯配体和制备方法及应用 |
| GB0700622D0 (en) * | 2007-01-12 | 2007-02-21 | Johnson Matthey Plc | Process for preparing cationic rhodium complexes |
| GB0812290D0 (en) * | 2008-07-04 | 2008-08-13 | Johnson Matthey Plc | Process for preparing cationic rhodium complexes |
| CN102459292B (zh) | 2009-05-06 | 2015-11-25 | 约翰森·马瑟公开有限公司 | 金属配合物的制备 |
| GB201320869D0 (en) | 2013-11-26 | 2014-01-08 | Johnson Matthey Plc | Process |
| US9308527B2 (en) | 2014-03-17 | 2016-04-12 | Eastman Chemical Company | Phosphorous compounds useful as ligands and compositions and methods regarding them |
| PT108303A (pt) | 2015-03-20 | 2016-09-20 | Sapec Agro S A | Processo de produção de (s)-metolacloro |
| CN110548546A (zh) * | 2018-05-31 | 2019-12-10 | 中国科学院大连化学物理研究所 | 一种铱/线型膦-亚磷酰胺体系催化亚胺不对称氢化方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19936473A1 (de) | 1999-08-03 | 2001-02-08 | Studiengesellschaft Kohle Mbh | Neue chirale Phosphorliganden und ihre Verwendung in der Herstellung optisch aktiver Produkte |
| US6590115B2 (en) * | 2000-09-29 | 2003-07-08 | Eastman Chemical Company | Phosphino-aminophosphines |
| US6620954B1 (en) * | 2002-03-25 | 2003-09-16 | Eastman Chemical Company | Phosphinometallocenylamides as novel ligands for asymmetric catalysis |
| GB0400720D0 (en) * | 2004-01-14 | 2004-02-18 | Stylacats Ltd | Novel ferrocene-based phosphorus chiral phosphines |
| US6906212B1 (en) * | 2004-06-25 | 2005-06-14 | Eastman Chemical Company | Phosphine-phosphoramidite compounds |
| US6939981B1 (en) * | 2004-06-25 | 2005-09-06 | Eastman Chemical Company | Ruthenium complexes of phosphine-aminophosphine ligands |
| US6906213B1 (en) * | 2004-06-25 | 2005-06-14 | Eastman Chemical Company | Preparation of aminophosphines |
-
2004
- 2004-06-25 US US10/876,387 patent/US6906212B1/en not_active Expired - Lifetime
-
2005
- 2005-06-16 EP EP05761206A patent/EP1758844B1/en not_active Expired - Lifetime
- 2005-06-16 AT AT05761206T patent/ATE491678T1/de not_active IP Right Cessation
- 2005-06-16 DE DE602005025346T patent/DE602005025346D1/de not_active Expired - Lifetime
- 2005-06-16 WO PCT/US2005/021373 patent/WO2006012045A1/en not_active Ceased
- 2005-06-16 JP JP2007518135A patent/JP2008504261A/ja not_active Withdrawn
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