HUP0100419A2 - Átmenetifémekkel katalizált eljárás, a katalizátorokhoz alkalmazható királis ligandumok, és előállításuk - Google Patents
Átmenetifémekkel katalizált eljárás, a katalizátorokhoz alkalmazható királis ligandumok, és előállításukInfo
- Publication number
- HUP0100419A2 HUP0100419A2 HU0100419A HUP0100419A HUP0100419A2 HU P0100419 A2 HUP0100419 A2 HU P0100419A2 HU 0100419 A HU0100419 A HU 0100419A HU P0100419 A HUP0100419 A HU P0100419A HU P0100419 A2 HUP0100419 A2 HU P0100419A2
- Authority
- HU
- Hungary
- Prior art keywords
- catalyzes
- preparation
- transition metal
- chiral ligands
- catalyzed reaction
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title abstract 3
- 238000006555 catalytic reaction Methods 0.000 title 1
- 230000007704 transition Effects 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- -1 imidate ester Chemical class 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
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- 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
- B01J31/1805—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 nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
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- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
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- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
- C07C45/505—Asymmetric hydroformylation
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
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- 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
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
- B01J2231/325—Cyclopropanations
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
- B01J2231/326—Diels-Alder or other [4+2] cycloadditions, e.g. hetero-analogues
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
- B01J2231/342—Aldol type reactions, i.e. nucleophilic addition of C-H acidic compounds, their R3Si- or metal complex analogues, to aldehydes or ketones
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/348—1,4-additions, e.g. conjugate additions
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4261—Heck-type, i.e. RY + C=C, in which R is aryl
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- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/44—Allylic alkylation, amination, alkoxylation or analogues
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- 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
- B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
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- 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
- B01J2531/821—Ruthenium
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- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
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- B01J2531/824—Palladium
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- 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
- B01J2531/827—Iridium
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- C07B2200/07—Optical isomers
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- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A találmány szerinti oxazolini-amino-csoportokattartalmazó királis ligandumok az átmeneti fémekkel aszimmetrikusreakciókban megnövelt enantioszelektivitású katalizátort képeznek. Akirális ligandumok szerkezete (I), (II) (III) vagy (IV) általánosképletnek felel meg, ahol R, R1, R2, R3, R4, R5, R6 és R7 jelentéseegymástól függetlenül hidrogénatom, alkilcsoport, arilcsoport,helyettesített alkilcsoport vagy helyettesített arilcsoport, ahol R1,R2, R3 és R4 közül bármelyik két helyettesítő egymással gyűrűsszerkezetté kapcsolódhat össze, és ahol R5, R6 és R7 közül bármelyikkét helyettesítő egymással gyűrűs szerkezetté kapcsolódhat össze, és nértéke 1 vagy 2. A találmány szerint az aszimmetrikus reakcióbanmegnövelt enantioszelektivitású katalizátor előállítása során imidát-észtert királis alkohollal redukálnak. Ó
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US6550297P | 1997-11-12 | 1997-11-12 | |
PCT/US1998/024036 WO1999024410A1 (en) | 1997-11-12 | 1998-11-12 | Transition metal-catalyzed reactions based on chiral amine oxazolinyl ligands |
Publications (2)
Publication Number | Publication Date |
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HUP0100419A2 true HUP0100419A2 (hu) | 2001-05-28 |
HUP0100419A3 HUP0100419A3 (en) | 2001-10-29 |
Family
ID=22063174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU0100419A HUP0100419A3 (en) | 1997-11-12 | 1998-11-12 | Transition metal-catalyzed reaction, chiral ligands for these catalyzes and their preparation |
Country Status (14)
Country | Link |
---|---|
US (2) | US6255493B1 (hu) |
EP (1) | EP1030849A1 (hu) |
JP (1) | JP2001522838A (hu) |
KR (1) | KR20010031960A (hu) |
CN (1) | CN1278801A (hu) |
AU (1) | AU1398199A (hu) |
BR (1) | BR9814167A (hu) |
CA (1) | CA2308415A1 (hu) |
HU (1) | HUP0100419A3 (hu) |
IL (1) | IL135854A0 (hu) |
PL (1) | PL340767A1 (hu) |
TR (1) | TR200001333T2 (hu) |
WO (1) | WO1999024410A1 (hu) |
YU (1) | YU29300A (hu) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1030849A1 (en) * | 1997-11-12 | 2000-08-30 | The Pennsylvania State University | Transition metal-catalyzed reactions based on chiral amine oxazolinyl ligands |
US6239285B1 (en) | 1998-02-06 | 2001-05-29 | Pfizer Inc | Process for making 5-lipoxygenase inhibitors having varied heterocyclic ring systems |
US6743921B2 (en) * | 2002-01-24 | 2004-06-01 | Dsm Catalytica Pharmaceuticals, Inc. | Process for the preparation of nonracemic syn-1-(4-hydroxy-phenyl)-2-(4-hydroxy-4-phenyl-piperidin-1-yl)-1-propanol compounds |
AU2002318538A1 (en) * | 2002-07-15 | 2004-02-02 | Nippon Soda Co., Ltd. | Ruthenium compounds, diamine ligands, and process for preparation of optically active alcohols |
CN100364981C (zh) * | 2003-01-29 | 2008-01-30 | 北京大学 | 手性二苯并[a,c]环庚二烯双噁唑啉配体化合物及其制备与应用 |
GB0313661D0 (en) * | 2003-06-13 | 2003-07-16 | Avecia Ltd | Process |
GB0316439D0 (en) | 2003-07-15 | 2003-08-20 | Johnson Matthey Plc | Catalysts |
GB0329284D0 (en) * | 2003-12-18 | 2004-01-21 | Avecia Ltd | Process |
ITPD20040115A1 (it) * | 2004-05-04 | 2004-08-04 | Univ Degli Studi Udine | Complessi di rutenio con 2-(amminometil)piridine e fosfine, loro preparazione ed uso come catalizzatori |
CN100348597C (zh) * | 2005-12-29 | 2007-11-14 | 上海交通大学 | 5,5’位连接的1, 1’-联苯类轴手性配体的合成方法 |
CN100425598C (zh) * | 2006-09-09 | 2008-10-15 | 合肥工业大学 | 一种手性噁唑啉及其制备方法 |
ITPD20070237A1 (it) | 2007-07-11 | 2009-01-12 | Univ Degli Studi Udine | Nuovi leganti della classe della benzo[h]chinolina e complessi di metalli di transizione che li contengono e uso di tali complessi come catalizzatori |
CN101773856B (zh) * | 2010-01-21 | 2012-06-27 | 北京理工大学 | 一种噁唑啉西佛碱配体金属络合物催化剂及其应用 |
CN102199130A (zh) * | 2011-03-22 | 2011-09-28 | 罗梅 | 一种手性噁唑啉的制备及合成方法 |
CN102206212B (zh) * | 2011-04-06 | 2013-07-03 | 罗梅 | 一种手性噁唑啉的制备及合成方法 |
CN104119288B (zh) * | 2013-04-26 | 2016-05-25 | 中国科学院大连化学物理研究所 | 一种含氮四齿有机配体的合成方法 |
CN105481622A (zh) * | 2015-12-14 | 2016-04-13 | 武汉凯特立斯科技有限公司 | 一种α-氧代-α,β-不饱和羧酸的不对称氢化方法 |
CN106588987B (zh) * | 2016-11-30 | 2019-09-24 | 上海师范大学 | 一种手性噁唑啉类nnp型配体及其合成方法和应用 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3192224A (en) * | 1963-03-11 | 1965-06-29 | Coastal Interchemical Company | Aminomethyl oxazolines and process of preparing same |
DE2220413A1 (de) * | 1972-04-26 | 1973-11-15 | Huels Chemische Werke Ag | 2-aminoalkylsubstituierte cyclische imidsaeureester und verfahren zu deren herstellung |
HU167760B (hu) * | 1972-10-20 | 1975-12-25 | ||
PT77428B (fr) * | 1982-10-05 | 1986-02-27 | Cortial | Procede pour preparer de nouvelles amino-2-substitue-5-oxazoli-nes-2 et des compositions les contenant |
DE19548399A1 (de) * | 1995-12-22 | 1997-06-26 | Basf Ag | Rutheniumkomplexe mit einem chiralen, zweizähnigen Phosphinoxazolin-Liganden zur enantioselektiven Transferhydrierung von prochiralen Ketonen |
EP1030849A1 (en) * | 1997-11-12 | 2000-08-30 | The Pennsylvania State University | Transition metal-catalyzed reactions based on chiral amine oxazolinyl ligands |
-
1998
- 1998-11-12 EP EP98957813A patent/EP1030849A1/en not_active Withdrawn
- 1998-11-12 WO PCT/US1998/024036 patent/WO1999024410A1/en not_active Application Discontinuation
- 1998-11-12 PL PL98340767A patent/PL340767A1/xx not_active Application Discontinuation
- 1998-11-12 AU AU13981/99A patent/AU1398199A/en not_active Abandoned
- 1998-11-12 KR KR1020007005068A patent/KR20010031960A/ko not_active Application Discontinuation
- 1998-11-12 IL IL13585498A patent/IL135854A0/xx unknown
- 1998-11-12 JP JP2000520424A patent/JP2001522838A/ja active Pending
- 1998-11-12 US US09/189,867 patent/US6255493B1/en not_active Expired - Lifetime
- 1998-11-12 HU HU0100419A patent/HUP0100419A3/hu unknown
- 1998-11-12 BR BR9814167-8A patent/BR9814167A/pt not_active Application Discontinuation
- 1998-11-12 YU YU29300A patent/YU29300A/sh unknown
- 1998-11-12 CN CN98811131A patent/CN1278801A/zh active Pending
- 1998-11-12 TR TR2000/01333T patent/TR200001333T2/xx unknown
- 1998-11-12 CA CA002308415A patent/CA2308415A1/en not_active Abandoned
-
2001
- 2001-05-04 US US09/848,227 patent/US6451727B2/en not_active Expired - Fee Related
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Publication number | Publication date |
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CN1278801A (zh) | 2001-01-03 |
US6451727B2 (en) | 2002-09-17 |
WO1999024410A1 (en) | 1999-05-20 |
CA2308415A1 (en) | 1999-05-20 |
TR200001333T2 (tr) | 2000-10-23 |
JP2001522838A (ja) | 2001-11-20 |
IL135854A0 (en) | 2001-05-20 |
US6255493B1 (en) | 2001-07-03 |
KR20010031960A (ko) | 2001-04-16 |
YU29300A (sh) | 2003-08-29 |
EP1030849A1 (en) | 2000-08-30 |
BR9814167A (pt) | 2000-09-26 |
AU1398199A (en) | 1999-05-31 |
HUP0100419A3 (en) | 2001-10-29 |
US20010044546A1 (en) | 2001-11-22 |
PL340767A1 (en) | 2001-02-26 |
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