Immobilizing a single pybox ligand onto a library of solid supports

Molecular Diversity

Volumn 6, Issue 2, 2003, Pages 93-105

  Cornejo, Alfonso ^a   Fraile, José M ^b   García, José I ^b   Gil, María J ^a   Martínez Merino, Víctor ^a   Mayoral, José A ^b  

^a PUBLIC UNIVERSITY OF NAVARRE   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

Asymmetric catalysis; Heterogeneous catalysis; Immobilization; Library of supports; Polymerization; Pybox; Sol gel synthesis

Indexed keywords

4 AMINOPHENOL; 4 HYDROXYBENZALDEHYDE; DIAZOACETIC ACID ETHYL ESTER; LIGAND; OXAZOLINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDINEBIS(OXAZOLINE); RUTHENIUM; SILANE; SILICON DIOXIDE; STYRENE; TRIETHOXYSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; COMPLEX FORMATION; CYCLOPROPANATION; IMMOBILIZATION; PRIORITY JOURNAL; SOLID STATE; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; OXAZOLES; PYRIDINES; RUTHENIUM; SILICON DIOXIDE;

EID: 0347719207     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006838.15630.97     Document Type: Article

References (28)

1. Blaser, H.-U., Enantioselective catalysis in fine chemicals production, Chem. Commun., (2003) 293-296.
2. De Vos, D. E., Vankelecom, I. F. J. and Jacobs, P. A. (eds.), Chiral Catalysts Immobilization and Recycling, Wiley-VCH, Weinheim, 2000.
3. Altava, B., Burguete, M. I., Fraile, J. M., García, J. I., Luis S. V., Mayoral, J. A. and Vicent, M. J., How important is the inert matrix of supported enantiomeric catalysts? Reversal of topicity with two polystyrene backbones, Angew. Chem. Int. Ed., 39 (2000) 1503-1506.
4. Rechavi, D. and Lemaire, M., Enantioselective catalysts using heterogeneous bis(oxazoline) ligands: which factors influence the enantioselectivity?, Chem. Rev., 102 (2002) 3467-3494.
5. Fraile, J. M., García, J. I., Mayoral, J. A., Tarnai, T. and Harmer, M. A., Bis(oxazoline)-copper complexes, supported by electrostatic interactions, as heterogeneous catalysts for enantioselective cyclopropanation reactions: influence of the anionic support, J. Catal., 186 (1999) 214-221.
6. Fernández, A. I., Fraile, J. M., García, J. I., Herrerías, C. I., Mayoral, J. A. and Salvatella, L., Reversal of enantioselectivity by change of solvent with clay-immobilized bis(oxazoline)-copper catalysts, Catal. Commun., 2 (2001) 165-170.
7. Fraile, J. M., García, J. I., Harmer, M. A., Herrerías, C. I., Mayoral, J. A., Reiser, O. and Werner, H., Immobilisation of bis(oxazoline)-copper complexes on clays and nanocomposites. Influence of different parameters on activity and selectivity, J. Mater. Chem., 12 (2002) 3290-3295.
8. Burguete, M. I., Fraile, J. M., García, J. I., García-Verdugo, E., Luis, S. V. and Mayoral, J. A., Polymer-supported bis(oxazoline)-copper complexes as catalysts in cyclopropanation reactions, Org. Lett., 2 (2000) 3905-3908.
9. Burguete, M. I., Fraile, J. M., García, J. I., García-Verdugo, E., Herrerías, C. I., Luis, S. V. and Mayoral, J. A., Bis(oxazoline)-copper complexes covalently bonded to insoluble support as catalysts in cyclopropanation reactions, J. Org. Chem., 66 (2001) 8893-8901.
10. Orlandi, S., Mandoli, A., Pini, D. and Salvadori, P., An insoluble polymer-bound bis-oxazoline copper(II) complex: a highly efficient heterogeneous catalyst for the enantioselective Mukaiyama aldol reaction, Angew. Chem. Int. Ed., 40 (2001) 2519-2521.
11. Hallman, K. and Moberg, C., Polymer-bound bis(oxazoline) as a chiral catalyst, Tetrahedron: Asymmetry, 12 (2001) 1475-1478.
12. Rechavi, D. and Lemaire, M., Heterogenization of a chiral bis(oxazoline) catalyst by grafting onto silica, Org. Lett., 3 (2001) 2493-2496.
13. Corma, A., García, H., Moussaif, A., Sabater, M. J., Zniber, R. and Redouane, A., Chiral copper(II) bisoxazoline covalently anchored to silica and mesoporous MCM-41 as a heterogeneous catalyst for the enantioselective Friedel-Crafts hydroxyalkylation, Chem. Commun., (2002) 1058-1059.
14. Nishiyama, H., Itoh, Y., Sugawara, Y., Matsumoto, H., Aoki, K. and Itoh, K., Chiral ruthenium(II)-bis(2-oxazolin-2-yl)pyridine complexes. Asymmetric catalytic cyclopropanation of olefins and diazoacetates, Bull. Chem. Soc. Jpn., 68 (1995) 1247-1262.
15. Nishiyama, H., Yamaguchi, S., Kondo, M. and Itoh, K., Electronic substituent effect of nitrogen ligand in catalytic asymmetric hydrosilylation of ketones: chiral 4-substituted bis(oxazolinyl)pyridines, J. Org. Chem., 57 (1992) 4306-4309.
16. 2-symmetric copper(II) complexes as chiral Lewis acids. Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde, J. Am. Chem. Soc., 121 (1999) 669-685.
17. Schaus, S. E. and Jacobsen, E. N., Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes, Org. Lett., 2 (2000) 1001-1004.
18. Iwasa, S., Maeda, H., Nishiyama, K., Tsushima, S., Tsukamoto, Y. and Nishiyama, H., A highly enantioselective 1,3-dipolar cycloaddition reaction in alcoholic media: Ni(II)-pybox-tipsom catalyst, Tetrahedron, 58 (2002) 8281-8287.
19. Cornejo, A., Fraile, J. M., García, J. I., Gil, M. J., Legarreta, G., Luis, S. V., Martínez-Merino, V. and Mayoral, J. A., The first immobilization of pyridine-bis(oxazoline) chiral ligands, Org. Lett., 4 (2002) 3927-3930.
20. Anderson, H., Jönsson, C. Moberg, C. and Stemme, G., Consecutive microcontact printing ligands for asymmetric catalysis in silicon channels, Sensors Actuators B 79 (2001) 78-84.
21. Armistead, C. G., Tyler, A. J., Hambleton, F. H., Mitchell, S. A. and Hockey, J. A., The surface hydroxylation of silica, J. Phys. Chem., 73 (1969) 3947-3953.
22. Blitz, J. P., Meverden, C. C. and Diebel III, R. E., Reactions of dibutylmagnesium with modified silica gel surfaces, Langmuir, 14 (1998) 1122-1129.
23. Adima, A., Moreau, J. J. E. and Man, M. W. C., Chiral organic-inorganic solids as enantioselective catalytic materials, J. Mater. Chem., 7 (1997) 2331-2333.
24. Adima, A., Moreau, J. J. E. and Man, M. W. C., Immobilization of rhodium complexes in chiral organic-inorganic hybrid materials, Chirality, 12 (2000) 411-420.
25. Hesemann, P. and Moreau, J. J. E., Novel silica-based hybrid materials incorporating binaphthyl units: a chiral matrix effect in heterogeneous asymmetric catalysis, Tetrahedron: Asymmetry, 11 (2000) 2183-2194.
26. Bied, C., Gauthier, D., Moreau, J. J. E. and Man, M. W. C., Preparation and characterization of new templated hybrid materials containing a chiral diamine ligand, J. Sol-Gel Sci. Tech., 20 (2001) 313-320.
27. Macquarrie, D. J., Jackson, D. B., Mdoe, J. E. G. and Clark, J. H., Organomodified hexagonal mesoporous silicates, New J. Chem., 23 (1999) 539-544.
28. Tanev, P. T. and Pinnavaia, T. J., Mesoporous silica molecular sieves prepared by ionic and neutral surfactant templating: a comparison of physical properties, Chem. Mater., 8 (1996) 2068-2079.