Highly efficient immobilization of Cinchona alkaloid derivatives to silica gel via click chemistry

Tetrahedron Letters

Volumn 47, Issue 49, 2006, Pages 8721-8726

  Kacprzak, Karol M ^a   Maier, Norbert M ^a   Lindner, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Chiral stationary phase (CSP); Cinchona alkaloids; Click chemistry; Enantioseparation; Immobilization

Indexed keywords

ACETONITRILE; ALKALOID DERIVATIVE; CARBAMIC ACID DERIVATIVE; CUPROUS ION; HYDROQUININE; IODIDE; SILICA GEL; SULFIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CINCHONA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; ROOM TEMPERATURE; STRUCTURE ANALYSIS;

CINCHONA;

EID: 33750492630     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.018     Document Type: Article

References (42)

1. In: De Vos D.E., Vankelecom I.F.J., and Jacobs P.A. (Eds). Chiral Catalyst Immobilization and Recycling (2000), Wiley-VCH, Weinheim
2. Kirschning A. Immobilized Catalysts. Solid Phases, Immobilization and Applications (2004), Springer, Berlin
3. Song Ch.E., and Lee L. Chem. Rev. 102 (2002) 3495
4. Busch K.W. Chiral Analysis (2006), Elsevier
5. In: Orellana G. (Ed). Frontiers in Chemical Sensors. Novel Principles and Techniques (2005), Springer, Berlin
6. Heise Ch., and Bier F.F. Top. Curr. Chem. 261 (2005) 1
7. In: Mannhold R., Kubinyi H., Folkers G., Bannwarth W., and Hinzen B. (Eds). Combinatorial Chemistry: From Theory to Application (2005), Wiley-VCH, Weinheim
8. In: Nicolaou K.C., Hanko R., and Hartwig W. (Eds). Handbook of Combinatorial Chemistry: Drugs, Catalysts, Materials (2002), Wiley-VCH, Weinheim
9. Krawinkler K.H., Gavioli E., Maier M.N., and Lindner W. Chromatographia 58 (2003) 555
10. Tornøe C.W., and Meldal M. In: Lebl M., and Houghten R.A. (Eds). Peptidotriazoles: Copper(I)-catalyzed 1,3-Dipolar Cycloadditions on Solid-phase (2001), American Peptide Society and Kluwer Academic Publishers, San Diego 263
11. Tornoe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057
12. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596
13. Kolb H.C., and Sharpless K.B. Drug Discov. Today 8 (2003) 1128
14. Bock V.D., Hiemstra H., and van Maarseveen J.H. Eur. J. Org. Chem. (2006) 51
15. Punna S., Kaltgrad E., and Finn M.G. Bioconjugate Chem. 16 (2005) 1536
16. Slater M., Snauko M., Svec F., and Frechet J.M.J. Anal. Chem. 78 (2006) 4969
17. To the best of our knowledge, efforts to functionalize the surfaces of silicon wafers has been the only related work:. Lummerstorfer T., and Hoffmann H. J. Phys. Chem. B 108 (2004) 3963
18. Hellriegel C., Skogsberg U., Albert K., Lämmerhofer M., Maier N.M., and Lindner W. J. Am. Chem. Soc. 126 (2004) 3809
19. Maier N.M., Schefzick S., Lombardo G.M., Feliz M., Rissanen K., Lindner W., and Lipkowitz K.B. J. Am. Chem. Soc. 124 (2002) 8611
20. Czerwenka C., Zhang M.M., Kahlig H., Maier N.M., Lipkowitz K.B., and Lindner W. J. Org. Chem. 68 (2003) 8315
21. Krawinkler K.H., Maier N.M., Sajovic E., and Lindner W. J. Chromatogr. A 1053 (2004) 119
22. Franco P., Lämmerhofer M., Klaus P.M., and Lindner W. J. Chromatogr. A 869 (2000) 111
23. Lämmerhofer M., and Lindner W. J. Chromatogr. A 741 (1996) 33
24. Kacprzak K., Grajewski J., and Gawroński J. Tetrahedron: Asymmetry 17 (2006) 1332
25. Kacprzak K., and Gawroński J. Chem. Commun. (2003) 1532
26. Kacprzak K., and Gawroński J. Synthesis (2001) 961
27. Tian S.-K., Chen Y., Hang J., Tang L., Mcdaid P., and Deng L. Acc. Chem. Res. 8 (2004) 518
28. Yoon T.P., and Jacobsen E.N. Science 299 (2003) 1691
29. Danelli T., Annunziata R., Benaglia M., Cinquini M., Cozzi F., and Tocco G. Tetrahedron: Asymmetry 14 (2003) 461
30. O'Donnell M.J. Acc. Chem. Res. 37 (2004) 506
31. Chinchilla R., Mazon P., and Najera C. Adv. Synth. Catal. 346 (2004) 1186
32. Song Ch.E., Yang J.W., and Ha H.-J. Tetrahedron: Asymmetry 8 (1997) 841
33. Attempts to immobilize of N-3,5-dinitrophenylcarbamoyl quinine onto mercaptopropyl-modified silica proceeded sluggishly and partial reduction of nitro groups was observed as a side reaction.
34. Kacprzak K., Migas M., Plutecka A., Rychlewska U., and Gawronski J. Heterocycles 65 (2005) 1931
35. Brunner H., Bügler J., and Nuber B. Tetrahedron: Asymmetry 6 (1995) 1699
36. Braje W.M., Frackenpohl J., Schrake O., Wartchow R., Beil W., and Hoffmann H.M.R. Helv. Chim. Acta 83 (2000) 777
37. 3 in DMSO was irradiated in a microwave reactor (CEM discover) for 5 min at 125 °C at 150 W, then cooled and worked up as above. CHN analysis: C 6.0%, H 1.4%, N 1.5% which corresponds to 0.36 mmol/g of loading.
38. All synthesized compounds (1-4) were prepared using commercially available reagents, characterized by NMR and MS spectra and were >95% pure (HPLC).
39. Chiral Technologies Europe http://www.chiral.fr.
40. General procedure for room-temperature click immobilization: A solution of CuI in acetonitrile (1-0.01 equiv of Cu(I), see Table 1) was quickly added to a mixture of azido silica gel (1 equiv), alkyne (0.9 equiv), DIPEA (3 equiv) in degassed acetonitrile (2 mL for 100 mg of silica gel). The vial was tightly sealed and shaken (180 rpm) at an ambient temperature for 2 days. The modified silica was then filtered and washed with acetonitrile, methanol, 2% aq EDTA solution, methanol-water mixture (1:1), 10% AcOH in methanol, and pure methanol. Vacuum dried material (12 h, 60 °C) was subjected to elemental analysis. Dihydroquinine tert-butylcarbamate (10 mol %) was employed as an internal standard and was used for HPLC monitoring of the reaction kinetics.
41. A similar protocol was employed for the efficient immobilization of 4 onto azido-modified polystyrene materials (prepared from commercially available Merrifield resin; 4.0 mmol chloromethyl groups/g), producing a loading level of 3.32 mmol Cinchona ligand/g. Azido-modified polystyrenes were also reported by other groups:. Loeber S., and Gmeiner P. Tetrahedron 60 (2004) 8699
42. Blass B.E., Coburn K.R., Faulkner A.L., Seibel W.L., and Srivastava A. Tetrahedron Lett. 44 (2004) 2153