Skip to main content
SpringerLink
Log in

Non-covalent Immobilization of Catalysts Based on Chiral Diazaligands

  • Chapter
  • First Online:
Chiral Diazaligands for Asymmetric Synthesis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 15))

Abstract

The immobilization of chiral catalysts through non-covalent methods, as opposed to covalent immobilization, allows an easier preparation of chiral heterogeneous catalysts with, in principle, less influence of the support on the conformational preferences of the catalytic complex. In this review the different possibilities for immobilization without forming a covalent bond between the chiral diazaligand and the support, which can be either solid or liquid, are presented.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Blaser HU, Studer M (1999) Heterogeneous catalysis. In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis, vol III. Springer, Berlin Heidelberg New York, p 1353

    Google Scholar 

  2. De Vos DE, Vankelecom IFJ, Jacobs PA (eds) (2000) Chiral catalysts immobilization and recycling. Wiley-VCH, Weinheim

    Google Scholar 

  3. Oehme G (1999) Catalyst immobilization: two-phase systems. In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis, vol III. Springer, Berlin Heidelberg New York, p 1377

    Google Scholar 

  4. Blaser HU, Studer M (1999) Catalyst immobilization: solid supports. In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis, vol III. Springer, Berlin Heidelberg New York, p 1367

    Google Scholar 

  5. Pozzi G, Cinato F, Montanari F, Quici S (1998) Chem Commun 877

    Google Scholar 

  6. Pozzi G, Cavazzini M, Cinato F, Montanari F, Quici S (1999) Eur J Org Chem 1947

    Google Scholar 

  7. Cavazzini M, Manfredi A, Montanari F, Quici S, Pozzi G (2000) Chem Commun 2171

    Google Scholar 

  8. Cavazzini M, Manfredi A, Montanari F, Quici S, Pozzi G (2001) Eur J Org Chem 4639

    Google Scholar 

  9. Cavazzini M, Pozzi G, Quici S, Shepperson I (2003) J Mol Catal A 204:433

    Article  Google Scholar 

  10. Maillard D, Nguefack C, Pozzi G, Quici S, Valadé B, Sinou D (2000) Tetrahedron: Asymmetry 11:2881

    Article  Google Scholar 

  11. Millard D, Pozzi G, Quici S, Sinou D (2002) Tetrahedron 58:3971

    Article  Google Scholar 

  12. Cavazzini M, Quici S, Pozzi G (2002) Tetrahedron 58:3943

    Article  Google Scholar 

  13. Shepperson I, Cavazzini M, Pozzi G, Quici S (2004) J Fluorine Chem 125:175

    Article  Google Scholar 

  14. Song CE, Roh EJ (2000) Chem Commun 837

    Google Scholar 

  15. Song CE, Roh CR, Roh EJ, Choo DJ (2000) Chem Commun 1743

    Google Scholar 

  16. Oh CR, Choo DJ, Shim WH, Lee DH, Roh EJ, Lee S, Song CE (2003) Chem Commun 1100

    Google Scholar 

  17. Baleizão C, Gigante B, Garcia H, Corma A (2002) Green Chem 4:272

    Article  Google Scholar 

  18. Baleizão C, Gigante B, Garcia H, Corma A (2003) Tetrahedron Lett 44:6813

    Article  Google Scholar 

  19. Vankelecom IFJ, Tas D, Parton RF, Van de Vyver V, Jacobs PA (1996) Angew Chem Int Ed 35:1346

    Article  Google Scholar 

  20. Janssen KBM, Laquiere I, Dehaen W, Parton RF, Vankelecom IFJ, Jacobs PA (1997) Tetrahedron: Asymmetry 8:3481

    Article  Google Scholar 

  21. Ogunwumi SB, Bein T (1997) Chem Commun 901

    Google Scholar 

  22. Sabater MJ, Corma A, Domenech A, Fornés V, García H (1997) Chem Commun 1285

    Google Scholar 

  23. Gbery G, Zsigmond A, Balkus Jr KJ (2001) Catal Lett 74:77

    Article  Google Scholar 

  24. Kahlen W, Wagner HH, Hölderich WF (1998) Catal Lett 54:85

    Google Scholar 

  25. Gigante B, Corma A, García H, Sabater MJ (2000) Catal Lett 68:113

    Article  Google Scholar 

  26. Doménech A, Formentin P, García H, Sabater MJ (2000) Eur J Inorg Chem 1339

    Google Scholar 

  27. Frunza L, Kosslich H, Landmesser H, Höft E, Fricke R (1997) J Mol Catal A 123:179

    Article  Google Scholar 

  28. Zhou XG, Yu XQ, Huang JS, Li SG, Li LS, Che CM (1999) Chem Commun 1789

    Google Scholar 

  29. Dioos BML, Jacobs PA (2003) Tetrahedron Lett 44:8815

    Article  Google Scholar 

  30. Fraile JM, García JI, Massam J, Mayoral JA (1998) J Mol Catal A 136:47

    Google Scholar 

  31. Heinrichs C, Hölderich WF (1999) Catal Lett 58:75

    Article  Google Scholar 

  32. Schuster C, Hölderich WF (2000) Catal Today 60:193

    Article  Google Scholar 

  33. Schuster C, Möllmann E, Tompos A, Hölderich WF (2001) Catal Lett 74:69

    Article  Google Scholar 

  34. Piaggio P, McMorn P, Langham C, Bethell D, Bulman-Page PC, Hancock FE, Hutchings GJ (1998) New J Chem 1167

    Google Scholar 

  35. Piaggio P, Langham C, McMorn P, Bethell D, Bulman-Page PC, Hancock FE, Sly C, Hutchings GJ (2000) J Chem Soc Perkin Trans 2:143

    Google Scholar 

  36. Piaggio P, McMorn P, Murphy D, Bethell D, Bulman-Page PC, Hancock FE, Sly C, Kerton OJ, Hutchings GJ (2000) J Chem Soc Perkin Trans 2:2008

    Google Scholar 

  37. Kim GJ, Kim SH (1999) Catal Lett 57:139

    Article  Google Scholar 

  38. Kim GJ, Shin JH (1999) Catal Lett 63:83

    Article  Google Scholar 

  39. Xiang S, Zhang Y, Xin Q, Li C (2002) Chem Commun 2696

    Google Scholar 

  40. Kim JH, Kim GJ (2004) Catal Lett 92:123

    Article  Google Scholar 

  41. Kureshy RI, Khan NH, Abdi SHR, Ahmad I, Singh S, Jasra RV (2003) Catal Lett 91:207

    Article  Google Scholar 

  42. Kureshy RI, Khan NH, Abdi SHR, Ahmad I, Singh S, Jasra RV (2004) J Catal 221:234

    Article  Google Scholar 

  43. Bhattacharjee S, Anderson JA (2004) Chem Commun 554

    Google Scholar 

  44. Annunziata R, Benaglia M, Cinquini M, Cozzi F, Pozzi G (2003) Eur J Org Chem 1191

    Google Scholar 

  45. Fraile JM, García JI, Herrerías CI, Mayoral JA, Carré D, Vaultier M (2001) Tetrahedron: Asymmetry 12:1891

    Article  Google Scholar 

  46. Fraile JM, García JI, Herrerías CI, Mayoral JA, Gmough S, Vaultier M (2004) Green Chem 6:93

    Article  Google Scholar 

  47. Davies DL, Kandola SK, Patel RK (2004) Tetrahedron: Asymmetry 15:77

    Article  Google Scholar 

  48. Meracz I, Oh T (2003) Tetrahedron Lett 44:6465

    Article  Google Scholar 

  49. Fraile JM, García JI, Mayoral JA, Tarnai T (1997) Tetrahedron: Asymmetry 8:2089

    Article  Google Scholar 

  50. Fraile JM, García JI, Mayoral JA, Tarnai T (1998) Tetrahedron: Asymmetry 9:3997

    Article  Google Scholar 

  51. Alonso PJ, Fraile JM, García J, García JI, Martínez JI, Mayoral JA, Sánchez MC (2000) Langmuir 16:5607

    Article  Google Scholar 

  52. Fernández MJ, Fraile JM, García JI, Mayoral JA, Burguete MI, García-Verdugo E, Luis S, Harmer MA (2000) Topics Catal 13:303

    Article  Google Scholar 

  53. Fraile JM, García JI, Mayoral JA, Tarnai T, Harmer M (1999) J Catal 186:214

    Article  Google Scholar 

  54. Fraile JM, García JI, Herrerías CI, Mayoral JA, Harmer MA (2004) J Catal 221:532

    Article  Google Scholar 

  55. Fraile JM, García JI, Harmer M, Herrerías CI, Mayoral JA (2001) J Mol Catal A165:211

    Article  Google Scholar 

  56. Fraile JM, García JI, Harmer MA, Herrerias CI, Mayoral JA, Reiser O, Warner H (2002) J Mater Chem 12:3290

    Article  Google Scholar 

  57. Fraile JM, García JI, Herrerías CI, Mayoral JA, Reiser O, Socuellamos A, Werner H (2004) Chem Eur J 10:2997

    Article  Google Scholar 

  58. Fernández AI, Fraile JM, García JI, Herrerías CI, Mayoral JA, Salvatella L (2001) Catal Commun 2:165

    Article  Google Scholar 

  59. Cornejo A, Fraile JM, García JI, Gil MJ, Herrerías CI, Legarreta G, Martínez-Merino V, Mayoral JA (2003) J Mol Catal A 196:101

    Article  Google Scholar 

  60. Langham C, Piaggio P, Bethell D, Lee DF, McMorn P, Bulman Page P, Willock DJ, Sly C, Hancock FE, King F, Hutchings GJ (1998) Chem Commun 1601

    Google Scholar 

  61. Langham C, Bethell D, Lee DF, McMorn P, Bulman Page P, Willock DJ, Sly C, Hancock FE, King F, Hutchings GJ (1999) Appl Catal A 182:85

    Article  Google Scholar 

  62. Taylor S, Gullick J, McMorn P, Bethell D, Bulman Page P, Hancock FE, King F, Hutchings GJ (2001) J Chem Soc Perkin Trans 2:1724

    Google Scholar 

  63. Taylor S, Gullick J, McMorn P, Bethell D, Bulman Page P, Hancock FE, King F, Hutchings GJ (2001) J Chem Soc Perkin Trans 2:1714

    Google Scholar 

  64. Gullick J, Taylor S, McMorn P, Bethell D, Bulman Page P, Hancock FE, King F, Hutchings GJ (2002) J Mol Catal A 180:85

    Article  Google Scholar 

  65. Taylor S, Gullick J, McMorn P, Bethell D, Bulman Page P, Hancock FE, King F, Hutchings GJ (2003) Topics Catal 24:43

    Article  Google Scholar 

  66. Gullick J, Taylor S, Ryan D, McMorn P, Coogan M, Bethell D, Bulman Page P, Hancock FE, King F, Hutchings GJ (2003) Chem Commun 2808

    Google Scholar 

  67. Taylor S, Gullick J, Galea N, McMorn P, Bethell D, Bulman Page P, Hancock FE, King F, Willock DJ, Hutchings GJ (2003) Topics Catal 25:81

    Article  Google Scholar 

  68. Wan Y, McMorn P, Hancock FE, King F, Hutchings GJ (2003) Catal Lett 91:145

    Article  Google Scholar 

  69. Caplan NA, Hancock FE, Bulman Page P, Hutchings GJ (2004) Angew Chem Int Ed 43:1685

    Article  Google Scholar 

  70. O'Leary P, Krosveld NP, De Jong KP, van Koten G, Klein Gebbink RJM (2004) Tetrahedron Lett 45:3177

    Article  Google Scholar 

  71. Gamez P, Fache F, Lemaire M (1994) Bull Soc Chim Fr 31:600

    Google Scholar 

  72. Ferrand A, Bruno M, Tommasino ML, Lemaire M (2002) Tetrahedron: Asymmetry 13:1379

    Article  Google Scholar 

  73. Zsigmond A, Bogár K, Notheisz F (2002) Catal Lett 83:55

    Article  Google Scholar 

  74. Zsigmond A, Bogár K, Notheisz F (2003) J Catal 213:103

    Article  Google Scholar 

  75. Alcón MJ, Corma A, Iglesias M, Sánchez F (2002) J Mol Catal A 178:253

    Article  Google Scholar 

  76. Yu HB, Hu QS, Pu L (2000) Tetrahedron Lett 41:1681

    Article  Google Scholar 

  77. Yu HB, Hu QS, Pu L (2000) J Am Chem Soc 112:6500

    Article  Google Scholar 

  78. Zhang R, Yu WY, Wong KY, Che CM (2001) J Org Chem 66:8145

    Article  PubMed  Google Scholar 

  79. Zhang JL, Liu YL, Che CM (2002) Chem Commun 2906

    Google Scholar 

  80. Yin MY, Yuan GL, Wu YQ, Huang MH, Jiang YY (1999) J Mol Catal A 147:93

    Article  Google Scholar 

  81. Xue L, Zhou DJ, Tang L, Ji XF, Huang MY, Jiang YY (2004) React Funct Polym 58:117

    Article  Google Scholar 

  82. Yuan GL, Yin MY, Jiang TT, Huang MY, Jiang YY (2000) J Mol Catal A 159:45

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Instituto Universitario de Catálisis Homogénea, Facultad de Ciencias, Universidad de Zaragoza--C.S.I.C., 50009, Zaragoza, Spain

    José M. Fraile, José I. García & José A. Mayoral

Authors
  1. José M. Fraile
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. José I. García
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. José A. Mayoral
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to José A. Mayoral .

Editor information

Marc Lemaire Pierre Mangeney

Rights and permissions

Reprints and permissions

About this chapter

Cite this chapter

Fraile, J.M., García, J.I., Mayoral, J.A. Non-covalent Immobilization of Catalysts Based on Chiral Diazaligands. In: Lemaire, M., Mangeney, P. (eds) Chiral Diazaligands for Asymmetric Synthesis. Topics in Organometallic Chemistry, vol 15. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b136350

Download citation

Publish with us

Policies and ethics

Search

Navigation