Bis(oxazoline)-copper complexes supported by electrostatic interactions: Scope and limitations

Journal of Catalysis

Volumn 221, Issue 2, 2004, Pages 532-540

  Fraile, José M ^a   García, José I ^a   Herrerías, Clara I ^a   Mayoral, José A ^a   Harmer, Mark A ^b  

^a UNIVERSITY OF ZARAGOZA   (Spain)

^b DUPONT COMPANY   (United States)

Author keywords

Enantioselective cyclopropanation; Immobilized chiral catalysts

Indexed keywords

2,2' ISOPROPYLIDENEBIS(4 TERT BUTYL 2 OXAZOLINE); ACETIC ACID DERIVATIVE; AMMONIUM DERIVATIVE; CATION; COPPER COMPLEX; COPPER ION; DIAZOACETIC ACID ETHYL ESTER; LIGAND; MENTHYL DIAZOACETATE; METHANOL; NITROETHANE; OXAZOLINE DERIVATIVE; SOLVENT; STYRENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CATION EXCHANGE; CHIRALITY; CYCLOPROPANATION; ELECTRICITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; SOLID; SOLUBILITY;

EID: 0742290029     PISSN: 00219517     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jcat.2003.09.017     Document Type: Article

References (60)

1. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;Wiley, New York.
2. Jacobsen E.N., Pfaltz A., Yamamoto H. Comprehensive Asymmetric Catalysis. 1999;Springer, Berlin.
3. Blaser H.-U. Tetrahedron: Asymm. 3:1991;843.
4. Blaser H.-U., Müller M. Stud. Surf. Sci. Catal. 59:1991;73.
5. Blaser H.-U., Pugin B. Jannes G., Dubois V. Chiral Reactions in Heterogeneous Catalysis. 1995;33 Plenum, New York.
6. De Vos D.E., Vankelecom I.F.J., Jacobs P.A. Chiral Catalysts Immobilization and Recycling. 2000;Wiley-VCH, Weinheim.
7. See, for example Fraile J.M., García J.I., Mayoral J.A., Royo A.J. Tetrahedron: Asymm. 7:1996;2263.
8. Mazzei M., Marconi W., Riocci M. J. Mol. Catal. 9:1980;381.
9. Shimazu S., Ro K., Sento P., Ichikuni N., Uematsu T. J. Mol. Catal. A. 107:1996;297.
10. Sento T., Shimazu S., Ichikuni N., Uematsu T. Chem. Lett. 1998;1191.
11. Sento T., Shimazu S., Ichikuni N., Uematsu T. J. Mol. Catal. A. 137:1999;263.
12. Margalef-Català R., Claver C., Salagre P., Fernández E. Tetrahedron: Asymm. 11:2000;1469.
13. Selke R., Häupke H., Krause H.W. J. Mol. Catal. 56:1989;315.
14. Selke R., Capka M. J. Mol. Catal. 63:1990;319.
15. Brunner H., Bielmeier E., Wiehl J. J. Organomet. Chem. 384:1990;223.
16. Toth I., Hanson B.E., Davis M.E. J. Organomet. Chem. 397:1990;109.
17. Toth I., Hanson B.E. J. Mol. Catal. 71:1992;365.
18. Wagner H.H., Hausmann H., Hölderich W.F. J. Catal. 203:2001;150.
19. Fraile J.M., García J.I., Massam J., Mayoral J.A. J. Mol. Catal. A. 136:1998;47.
20. Piaggio P., McMorn P., Langham C., Bethell D., Bulman-Page P.C., Hancock F.E., Hutchings G.J. New J. Chem. 23:1998;1167.
21. Kim G.-J., Kim S.-H. Catal. Lett. 57:1999;139.
22. Piaggio P., Langham C., McMorn P., Bethell D., Bulman-Page P.C., Hancock F.E., Sly C., Hutchings G.J. J. Chem. Soc., Perkin Trans. 2:2000;143.
23. Piaggio P., McMorn P., Murphy D., Bethell D., Bulman-Page P.C., Hancock F.E., Sly C., Kerton O.J., Hutchings G.J. J. Chem. Soc., Perkin Trans. 2:2000;2008.
24. For some reviews on this subject see Rechavi D., Lemaire M. Chem. Rev. 102:2002;3467.
25. Jönsson C., Hallman K., Andersson H., Stemme G., Malkoch M., Malmström E., Hult A., Moberg C. Bioorg. Med. Chem. Lett. 12:2002;1857.
26. Glos M., Reiser O. Org. Lett. 2:2000;2045.
27. Annunziata R., Benaglia M., Cinquini M., Cozzi F., Pitillo M. J. Org. Chem. 66:2001;3160.
28. Burguete M.I., Fraile J.M., García J.I., García-Verdugo E., Luis S.V., Mayoral J.A. Org. Lett. 2:2000;3905.
29. Orlandi S., Mandoli A., Pini D., Salvadori P. Angew. Chem. Int. Ed. 40:2001;2519.
30. Hallman K., Moberg C. Tetrahedron: Asymm. 12:2001;1475.
31. Burguete M.I., Díez-Barra E., Fraile J.M., García J.I., García-Verdugo E., González R., Herrerías C.I., Luis S.V., Mayoral J.A., Sánchez-Verdú P. Bioorg. Med. Chem. Lett. 12:2002;1821.
32. Díez-Barra E., Fraile J.M., García J.I., García-Verdugo E., Herrerías C.I., Luis S.V., Mayoral J.A., Sánchez-Verdú P., Tolosa J. Tetrahedron: Asymm. 14:2003;773.
33. Burguete M.I., Fraile J.M., García J.I., García-Verdugo E., Herrerías C.I., Luis S.V., Mayoral J.A. J. Org. Chem. 66:2001;8893.
34. Rechavi D., Lemaire M. Org. Lett. 3:2001;2493.
35. Rechavi D., Lemaire M. J. Mol. Catal. A. 182-183:2002;239.
36. Clarke R.J., Shannon I.J. Chem. Commun. 2001;1936.
37. Park J.K., Kim S.-W., Hyeon T., Kim B.M. Tetrahedron: Asymm. 12:2001;2931.
38. Corma A., García H., Moussaif A., Sabater M.J., Zniber R., Redouane A. Chem. Commun. 2002;1058.
39. Fraile J.M., García J.I., Mayoral J.A., Tarnai T. Tetrahedron: Asymm. 8:1997;2089.
40. Fraile J.M., García J.I., Mayoral J.A., Tarnai T. Tetrahedron: Asymm. 9:1998;3997.
41. Alonso P.J., Fraile J.M., García J., García J.I., Martínez J.I., Mayoral J.A., Sánchez M.C. Langmuir. 16:2000;5607.
42. Fernández A.I., Fraile J.M., García J.I., Herrerías C.I., Mayoral J.A., Salvatella L. Catal. Commun. 2:2001;165.
43. Fraile J.M., García J.I., Mayoral J.A., Tarnai T., Harmer M.A. J. Catal. 186:1999;214.
44. Fernández M.J., Fraile J.M., García J.I., Mayoral J.A., Burguete M.I., García-Verdugo E., Luis S.V., Harmer M.A. Top. Catal. 13:2000;303.
45. Fraile J.M., García J.I., Herrerías C.I., Mayoral J.A., Harmer M.A. J. Mol. Catal. A. 165:2001;211.
46. Langham C., Piaggio P., Bethell D., Lee D.F., McMorn P., Bulman-Page P.C., Willock D.J., Sly C., Hancock F.E., King F., Hutchings G.J. Chem. Commun. 1998;1601.
47. Langham C., Taylor S., Bethell D., McMorn P., Bulman-Page P.C., Willock D.J., Sly C., Hancock F.E., King F., Hutchings G.J. J. Chem. Soc., Perkin Trans. 2:1999;1043.
48. Langham C., Bethell D., Lee D.F., McMorn P., Bulman-Page P.C., Willock D.J., Sly C., Hancock F.E., King F., Hutchings G.J. Appl. Catal. A. 182:1999;1601.
49. Taylor S., Gullick J., McMorn P., Bethell D., Bulman-Page P.C., Hancock F.E., King F., Hutchings G.J. J. Chem. Soc., Perkin Trans. 2:2001;1724.
50. Gullick J., Taylor S., McMorn P., Bethell D., Bulman-Page P.C., Hancock F.E., King F., Hutchings G.J. J. Mol. Catal. A. 180:2002;85.
51. Fraile J.M., García J.I., Harmer M.A., Herrerías C.I., Mayoral J.A., Reiser O., Werner H. J. Mater. Chem. 12:2002;3290.
52. Evans D.A., Woerpel K.A., Hinman M.M., Faul M.M. J. Am. Chem. Soc. 113:1991;726.
53. Evans D.A., Woerpel K.A., Scott M.J. Angew. Chem. Int. Ed. Engl. 31:1992;430.
54. Fraile J.M., García J.I., Mayoral J.A., Tarnai T. J. Mol. Catal. A. 144:1999;85.
55. Harmer M.A., Farneth W.E., Sun Q. J. Am. Chem. Soc. 118:1996;7708.
56. Harmer M.A., Sun Q., Michalczyk M.J., Yang Z. Chem. Commun. 1997;1803.
57. Evans D.A., Miller S.J., Lectka T., von Matt P. J. Am. Chem. Soc. 121:1999;7559.
58. Fritschi H., Leutenegger U., Pfaltz A. Helv. Chim. Acta. 71:1988;1553.
59. Lowenthal R.E., Abiko A., Masamune S. Tetrahedron Lett. 31:1990;6005.
60. Bedekar A.V., Koroleva E.B., Andersson P.G. J. Org. Chem. 62:1997;2518.