(19)
(11) EP 0 895 992 B8

(12) CORRECTED EUROPEAN PATENT SPECIFICATION
Note: Bibliography reflects the latest situation

(15) Correction information:
Corrected version no 1 (W1 B1)

(48) Corrigendum issued on:
02.09.2009 Bulletin 2009/36

(45) Mention of the grant of the patent:
10.06.2009 Bulletin 2009/24

(21) Application number: 98114643.4

(22) Date of filing: 04.08.1998
(51) International Patent Classification (IPC): 
C07D 263/12(2006.01)
C07C 69/747(2006.01)
 C07C 237/06(2006.01)

(54)

Copper complexes of optically active bisoxazolines as enantioselective catalysts in cyclopropanation reactions

Kupferkomplexe optisch aktiver Bisoxazoline als enantioselektive Katalysatoren bei Cyclopropanierungsreaktionen

Complexes de cuivre de bisoxazolines optiquement actives comme catalyseurs énantiosélectives pour les réactions de cyclopropanation

(84) Designated Contracting States:
BE CH DE FR GB IT LI NL

(30) Priority: 05.08.1997 JP 21041797

(43) Date of publication of application:
10.02.1999 Bulletin 1999/06

(73) Proprietor: Sumitomo Chemical Company, Limited
Tokyo 104-8260 (JP)

(72) Inventors:
  • Itagaki, Makoto
    Takatsuki-shi, Osaka (JP)
  • Suzukamo, Gohfu
    Suita-shi, Osaka (JP)

(74) Representative: Vossius & Partner 
Siebertstraße 4
81675 München
81675 München (DE)


(56) References cited: : 
   
  • E. J. COREY, K. ISHIHARA: "Highly enantioselective catalytic Diels-Alder addition promoted by a chiral bis(oxazoline)-magnesium complex" TETRAHEDRON LETTERS, vol. 33, no. 45, 1992, pages 6807-6810, XP002087670
  • S. E. DENMARK ET AL.: "Cyclopropanation with Diazomethane and Bis(oxazoline)palladium(II) Complexes" J. ORG. CHEM., vol. 62, no. 10, 1997, pages 3375-3389, XP000689793
  • S. BENNETT ET AL.: "Structure and Mechanism in Aerobic Alkene Epoxidations promoted by Ruthenium Complexes of Bis(dihydrooxazole) Ligands" J. CHEM. SOC. DALTON TRANS., vol. 3, 1995, pages 367-376, XP002087671
  • M. P. DOYLE ET AL.: "Enantioselektive Synthese von makrocyclischen Lactonen durch intramolekulare Cyclopropanierung von Diazoacetaten mit chiralen Cu(I)- und Rh(II)-Katalysatoren" ANGEW. CHEM., vol. 108, no. 12, 1996, pages 1439-1440, XP002087672
  • A. V. BEDEKAR, P. G. ANDERSSON: "A New Class of Bis-Oxazoline Ligands for the Cu-Catalysed Asymmetric Cyclopropanation of Olefins" TETRAHEDRON LETTERS, vol. 37, no. 23, 1996, pages 4073-4076, XP004029302
  • U. LEUTENEGGER ET AL.: "5-Aza-Semicorrins: A New Class of Bidentate Nitrogen Ligands for Enantioselective Catalysis" TETRAHEDRON, vol. 48, no. 11, 1992, pages 2143-2156, XP002087673
  • R. E. LOWENTHAL, S. MASAMUNE: "Asymmetric Copper-Catalyzed Cyclopropanation of Ttrisubstituted and Unsymmetrical cis-1,2-Disubstituted Olefins: Modified Bis-Oxazoline Ligands" TETRAHEDRON LETTERS, vol. 32, no. 50, 1991, pages 7373-7376, XP002087674
  • R. E. LOWENTHAL ET AL.: "Asymmetric Catalytic Cyclopropanation of Olefins: Bis-Oxazoline Copper Complexes" TETRAHEDRON LETTERS, vol. 31, no. 42, 1990, pages 6005-6008, XP002021203
  • D. MÜLLER ET AL.: "C(2)-Symmetric 4,4',5,5'-Tetrahydrobis(oxazoles) and 4,4',5,5'-Tetrahydro-2,2'-methylenebis[oxa zoles] as Chiral Ligands for Enantioselective Catalysis" HELV. CHIM. ACTA, vol. 74, no. 1, 1991, pages 232-240, XP002083087
  • A. BERNARDI ET AL.: "Enantioselective Mukaiyama-Michael Reactions of 2-Carbomethoxycyclopentenone Catalyzed by Chiral Bis(Oxazoline)-Cu(II) Complexes" TETRAHEDRON LETTERS, vol. 37, no. 49, 1996, pages 8921-8924, XP002087675
  • H. BRUNNER ET AL.: "Asymmetric catalysis, part 108. Copper catalysts with optically active ligands in the enantioselective Meerwein arylation of activated olefins" J. ORGANOMET. CHEM., vol. 541, no. 1-2, 1997, pages 89-95, XP004093706
  • J. M. TAKASC ET AL.: "Enantioselective Diels-Alder reactions: room temperature bis(oxazoline)-zinc, -magnesium, and -copper triflate catalysts" TETRAHEDRON: ASYMMETRY, vol. 8, no. 18, 1997, pages 3073-3078, XP004090515
  • A. BERNARDI ET AL.: "Enantioselective Mukaiyama-Michael Reactions of 2-Carbomethoxycyclopentenone Catalyzed by Chiral Bis(Oxazoline)-Cu(II) Complexes" TETRAHEDRON LETTERS, vol. 37, no. 49, 1996, pages 8921-8924, XP004068814
  • H. FALK, A. SUSTE: "On the Chemistry of Pyrrole Pigments, XCI: Copper Complexes of Pyridinologous Linear Tri- and Tetra-pyrroles as Cyclopropanation Catalysts" MONATSH. CHEM., vol. 125, no. 3, 1994, pages 325-334, XP002087676
 
Remarks:
The file contains technical information submitted after the application was filed and not included in this specification
 
Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention).