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WO2000061589A1 - Nouveaux ligands pour catalyse chirale - Google Patents

Nouveaux ligands pour catalyse chirale Download PDF

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Publication number
WO2000061589A1
WO2000061589A1 PCT/GB2000/000758 GB0000758W WO0061589A1 WO 2000061589 A1 WO2000061589 A1 WO 2000061589A1 GB 0000758 W GB0000758 W GB 0000758W WO 0061589 A1 WO0061589 A1 WO 0061589A1
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group
compound
formula
aryl
alkyl
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PCT/GB2000/000758
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English (en)
Inventor
Kevin Burgess
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Texas A&M University System
Texas A&M University
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Texas A&M University System
Texas A&M University
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Priority to AU29253/00A priority Critical patent/AU2925300A/en
Priority to EP00907776A priority patent/EP1165574A1/fr
Priority to JP2000610860A priority patent/JP2002541262A/ja
Priority to CA002369043A priority patent/CA2369043A1/fr
Publication of WO2000061589A1 publication Critical patent/WO2000061589A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07F9/653—Five-membered rings
    • 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
    • C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms

Definitions

  • the present invention relates to novel optically active phosphine oxazoline ligands, a process for the preparation thereof, metal complexes containing such novel ligands and the use of such complexes, or combinations of ligand with metal salts or complexes, as catalysts for asymmetric syntheses.
  • phosphine ligands which have played a significant role in the development of chiral catalysts are asymmetric phosphine ligands. Although over 1000 chiral diphosphine ligands have been prepared since the application of the DIPAMP ligand in the production of L-Dopa, only a few of these have the efficiency and selectivity of commercial applications. Some of the most well known phosphine ligands used include BI AP, BPPM, DEGPHOS, DIOP, Chiraphos, Skewphos, Duphos and BPE all of which acronyms are described by annotated references in e.g. WO 97/47633 and are incorporated herein by reference. However, these ligands have their disadvantages and are not ideal for all applications.
  • the present invention provides a phosphine oxazoline ligand of formula (I)
  • n, p, q, r are independently zero or 1 provided that at least one of n, p. q and r is 1 ;
  • X is O, S, Se, CH 2 , NH
  • Y is N, P, As, S; R is H; a straight - chain alkyl group, branched-chain alkyl group or a cyclo alkyl group optionally substituted by one or more groups independently selected from alkyl, aryl, halo, alkoxy, amine. phosphine and ether groups; an aryl group optionally substituted by one or more groups independently selected from alkyl. aryl, halo, alkoxy.
  • R 1 to R 13 are independently selected from H; a straight-chain alkyl group, a branched- chain alkyl group or a cyclo alkyl group optionally substituted by one or more groups independently selected from alkyl, aryl.
  • halo, alkoxy, amine, phosphine and ether groups an aryl group optionally substituted by one or more groups independently selected from alkyl, aryl, halo, alkoxy. amine, phosphine and ether groups; with the proviso that when m is 1, one of n, p, q and r is 1 the remaining three being zero, X is O, Y is P, R 1 and R 2 are both H, R 3 to R 11 if present are H, and R 12 and R 13 are both phenyl, then R is not CH 3 , C(CH 3 ) 3 , CHPh 2 , CPh 3 .
  • alkyl we mean a straight, branched or cyclo alkyl group having any number of carbon atoms, for example from 1 to 14 carbon atoms, such as from 1 to 10 carbon atoms.
  • the cyclo alkyl groups may have one or more rings in its structure e.g. adamantyl which has a fused tricyclic ring structure.
  • aryl * ' we mean an aromatic monovalent hydrocarbyl group which include wter alia aryl. alkaryl and aralkyl groups, for example phenyl. benzyl, naphthyl. etc.
  • m is 1 or 2; preferably 1.
  • n, p, q and r are 1. the remaining two may be zero or 1 ; preferably, two of n, p, q and r are 1, the remaining two are zero.
  • X is O, S, CH 2 or NH; preferably O.
  • Y is P, N or S; preferably P.
  • R may be derived from a hydrocarbyl group attached to a functional group of an organic compound or a polymer capable of giving rise to the grouping -N-C-X- in the ring structure of (I).
  • R may be an alkyl group of a polyacrylic acid, polymethacrylic acid, a polyacrylonitrile or a polyamide, all of which are polymers carrying a function group capable of giving rise to the grouping -N-C-X- in the ring structure of (I).
  • a first embodiment of the invention provides a compound of formula (IA)
  • m. X, Y. R. and R 1 to R ⁇ and R 12 and R 13 are as hereinbefore defined, provided that when m is 1.
  • X is O.
  • Y is P.
  • R 1 . R 2 . R 3 . R 4 and R 5 are H.
  • R 12 and R 13 are both phenyl. then R is not CH 3 . C(CH 3 ) 3 . CHPh 2 . CPh 3 . adamantyl. C 6 H 3 (t-Bu) 2 . ferrocenyl. CF 3 . Ph. C 6 H OMe. C 6 H 4 Me. C 6 H 4 NO 2 or C 6 F 5 .
  • a second embodiment of the invention provides a compound of formula (IB)
  • a third embodiment of the invention provides a compound of formula (IC)
  • a fourth embodiment of the invention provides a compound of formula (ID)
  • a particularly preferred embodiment of the invention provides a compound of the following structure: wherein R is a C alkyl group optionally substituted by one or more groups selected from phenyl and halo; where said substituent group is phenyl it may be optionally further substituted by one to five substituents selected from the group consisting of halo, CM alkyl. C M alkoxy or nitro; ferrocenyl or adamantyl; and R 12 and R 1 each of which may be a phenyl or cyclohexyl group.
  • Particularly preferred compounds include those of the following formulae:
  • R 14 and R 15 are alkyl groups which may be the same or different and Pro is a nitrogen protecting group, for example a butoxy carbonyl group (hereafter "BOC”), with a compound of formula (III)
  • R 16 is an alkyl group, for example ethyl
  • Hal is a halide group, for example chloride.
  • the reaction is carried out by the addition of for example gaseous HC1, in the presence of an alcohol, such as methanol to the compound of formula (II), followed by the addition of a compound of formula (III) in the presence of a base, for example triethylamine, in a suitable solvent such as dichloromethane.
  • L is a leaving group, such as e.g tosylate. iodide, triflate or bromide, with a compound of formula
  • LiYR R wherein Y, R ' and R , 13 are as hereinbefore defined.
  • the reaction is carried out in the presence of an organic solvent, such as THF, and with the addition of BH 3 .
  • the reaction is carried out with a suitable compound to give the desired leaving group.
  • a suitable compound for example if the leaving group is tosyl, the reaction is carried out with, e.g. tosyl chloride, in the presence of a base such as e.g. triethylamine, and a suitable solvent, such as e.g. dichloromethane.
  • a base such as e.g. triethylamine
  • a suitable solvent such as e.g. dichloromethane.
  • a catalytic amount of 4-dimethylaminopyridine (DMAP) may also be added.
  • a yet further aspect of the present invention provides a metal complex containing a ligand of formula (I) comprising a metal and optionally other ligands capable of stabilising the complex, e.g. chloride, acetate etc.
  • the metal is a transition metal; for example, the metal may be selected from the group consisting of Ni,
  • a metal complex of the present invention may be of use in any chemical reaction requiring an asymmetric catalyst. Examples of such reactions include but are not limited to Heck type reactions, Suzuki type reactions, allylation reactions, cross-coupling reactions, hydrogenations, hydroformylations and isomerisation reactions. Therefore, a still further aspect of the invention provides a metal complex of the invention for use in asymmetric catalytic reactions. Alternatively, the invention provides the use of a metal complex of the invention in asymmetric catalytic reactions. Alternatively, there is provided a method for performing an asymmetric catalytic reaction, said method comprising the use of a metal complex of the invention.
  • the metal complex of the invention may be formed in situ from a ligand of formula (I) and a suitable precursor complex or salt of a metal, which is preferably a transition metal as recited above. Therefore, a further aspect of the invention provides for the use of a ligand of formula (I) in combination with a metal complex or salt in asymmetric catalysis.
  • DMSO 169.1, 168.2, 70.0, 60.9, 48.5, 34.2, 14.9 and 13.9.
  • the ratio of the desired five- membered ring product (5) to the undesired six-membered ring product (6) was 6.4:3.6. Recrystallisation from heptane gave (5) as colourless needles (8.2 g, 48%). Spectral data for this sample were consistent with those given in the literature .
  • the protected phosphine (8) (500 mg, 1.17 mmol) was dissolved in 8 ml of methanol and cooled to 0°C. Gaseous HCl was bubbled through the reaction for 5-10 minutes. The methanol was removed under vacuum and the residue was dissolved in 8 ml of 1,2-dichloroethane. Triethylamine (1.5 ml, 9.3 mmol) and benzimidic acid ethyl ester hydrochloride 4 (230 mg, 1.24 mmol) were added, and the reaction was refluxed for 6 h.
  • the protected phosphine (8) (500 mg, 1.17 mmol) was dissolved in 8 ml of methanol and cooled to 0°C. Gaseous HCl was bubbled through the reaction for 5-10 minutes, and the methanol was removed under vacuum. The residue was dissolved in 8 ml of 1,2-dichloroethane and triethylamine (0.44 ml, 4.1 mmol), catalytic 4- dimethylaminopyridine (2 mg), then adamantanecarbonyl chloride (256 mg, 1.28 mmol) were added and reaction was stirred for 12 h.
  • This compound was prepared via the same method used for compound (lib), but beginning with 500 mg of (8), 117 mg (0.34 mmol, 30%) of the oxazoline (lie) was produced as colourless oil.
  • R f 0.68 ethyl acetate/hexane, 3:7 v/v).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne de nouveaux ligands d'oxazoline de phosphine représentés par la formule (I) dans laquelle m est 1, 2, 3 ou 4; n, p, q, r sont indépendamment zéro ou 1 à condition qu'au moins un élément parmi n, p, q et r soit 1; X est O, S, Se, CH2, NH; Y est N, P, As, S; R est H, un groupe alkyle à chaîne droite, un groupe alkyle à chaîne ramifiée ou un groupe alkyle cyclo éventuellement substitué par un ou plusieurs groupes indépendamment sélectionnés parmi les groupes alkyle, aryle, halo, alkoxy, amine, phosphine et éther, un groupe aryle éventuellement substitué par un ou plusieurs groupes indépendamment sélectionnés parmi les groupes alkyle, aryl, halo, alkoxy, amine, phosphine et éther, férrocényle, un groupe thioalkyle, un groupe thioaryle; ou R est dérivé d'un groupe hydrocarbyle lié à un groupe fonctionnel d'un composé organique ou un polymère pouvant générer le groupement -N-C-X- dans la structure cyclique de (I); R1 à R13 sont indépendamment sélectionnés parmi H, un groupe alkyle à chaîne droite, un groupe alkyle à chaîne ramifiée ou un groupe alkyle cyclo éventuellement substitué par un ou plusieurs groupes indépendamment sélectionnés parmi les groupes alkyle, aryle, halo, alkoxy, amine, phosphine et éther, un groupe aryle éventuellement substitué par un ou plusieurs groupes indépendamment sélectionnés parmi les groupes alkyle, aryle, halo, alkoxy, amine, phosphine et éther, à condition que lorsque m est 1, un élément parmi n, p, q et r soit 1, les trois autres étant zéro, X est O, Y est P, R1 et R2 sont tous les deux H, R3 à R11, si présents, sont H, et R?12 et R13¿ sont tous les deux phényle, R n'étant alors pas CH¿3?, C(CH3)3, CHPh2, CPh3, adamantyle, C6H3(t-Bu)2, ferrocényle, CF3, Ph, C6H4OMe, C6H4Me, C6H4NO2, ou C6F5. L'invention concerne également un procédé de préparation desdits ligands, des complexes métalliques contenant ces ligands et l'utilisation de ces complexes ou de combinaisons de ligands avec des sels ou des complexes métalliques, comme catalyseurs pour synthèses asymétriques.
PCT/GB2000/000758 1999-04-08 2000-03-03 Nouveaux ligands pour catalyse chirale Ceased WO2000061589A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU29253/00A AU2925300A (en) 1999-04-08 2000-03-03 Novel ligands for chiral catalysis
EP00907776A EP1165574A1 (fr) 1999-04-08 2000-03-03 Nouveaux ligands pour catalyse chirale
JP2000610860A JP2002541262A (ja) 1999-04-08 2000-03-03 キラル触媒用の新規リガンド
CA002369043A CA2369043A1 (fr) 1999-04-08 2000-03-03 Nouveaux ligands pour catalyse chirale

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9907895.8A GB9907895D0 (en) 1999-04-08 1999-04-08 Novel ligands for chiral catalysis
GB9907895.8 1999-04-08

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WO2000061589A1 true WO2000061589A1 (fr) 2000-10-19

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EP (1) EP1165574A1 (fr)
JP (1) JP2002541262A (fr)
CN (1) CN1353718A (fr)
AU (1) AU2925300A (fr)
CA (1) CA2369043A1 (fr)
GB (1) GB9907895D0 (fr)
WO (1) WO2000061589A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002187895A (ja) * 2000-09-21 2002-07-05 Solvias Ag ホスフィニト−オキサゾリン及び金属錯体

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1314673C (zh) * 2002-07-02 2007-05-09 中国科学院上海有机化学研究所 具有手性的多齿噁唑啉配体及其与主族金属或过渡金属的配合物、合成方法及其用途
CN102744106B (zh) * 2012-07-27 2014-08-06 山东师范大学 催化Suzuki偶联反应的钯催化剂、合成方法、应用及配位体
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

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EP0278621A1 (fr) * 1987-02-06 1988-08-17 Takeda Chemical Industries, Ltd. Dérivés substitués d'amine, leur préparation et leur application
WO1989012633A1 (fr) * 1988-06-20 1989-12-28 E.R. Squibb & Sons, Inc. Derives de benzazepine et de benzothiazepine
US4963671A (en) * 1989-11-20 1990-10-16 E. R. Squibb & Sons, Inc. Process for resolving chiral intermediates used in making calcium channel blockers
WO1994010127A1 (fr) * 1992-11-05 1994-05-11 Dompe' Farmaceutici S.P.A. Acides tartroniques, leurs ethers acetaliques et o-esters
DE4243030A1 (de) * 1992-12-18 1994-06-23 Basf Ag Iminverbindungen
WO1997048681A1 (fr) * 1996-06-20 1997-12-24 Smithkline Beecham Plc Derives du sulfonamide et leur utilisation dans le traitement des troubles du systeme nerveux central
WO1998050030A1 (fr) * 1997-05-07 1998-11-12 University Of Pittsburgh Inhibiteurs de proteines isoprenyle transferases

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002187895A (ja) * 2000-09-21 2002-07-05 Solvias Ag ホスフィニト−オキサゾリン及び金属錯体
EP1191030A3 (fr) * 2000-09-21 2002-07-17 Solvias AG Phosphinites-oxazolines et complexes métalliques
US6498256B2 (en) 2000-09-21 2002-12-24 Solvias Ag Phosphinite-oxazolines and metal complexes thereof
US6632954B2 (en) 2000-09-21 2003-10-14 Solvias Ag Phosphinite-oxazolines and metal complexes

Also Published As

Publication number Publication date
JP2002541262A (ja) 2002-12-03
GB9907895D0 (en) 1999-06-02
CN1353718A (zh) 2002-06-12
EP1165574A1 (fr) 2002-01-02
CA2369043A1 (fr) 2000-10-19
AU2925300A (en) 2000-11-14

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