Synthesis of acrylic polymer beads for solid-supported proline-derived organocatalysts

Organic Letters

Volumn 11, Issue 14, 2009, Pages 2968-2971

  Kristensen, Tor E ^a   Vestli, Kristian ^a   Fredriksen, Kim A ^a   Hansen, Finn K ^a   Hansen, Tore ^a  

^a UNIVERSITY OF OSLO   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; POLYMETHACRYLIC ACID DERIVATIVE; PROLINAMIDE; PROLINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; POLYMETHACRYLIC ACIDS; PROLINE; STEREOISOMERISM;

EID: 67650333080     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901134v     Document Type: Article

References (30)

1. Kondo, K.; Yamano, T.; Takemoto, K. Makromol. Chem 1985, 786, 1781.
2. (a) Benaglia, M.; Celentano, G.; Cozzi, F. Adv. Synth. Catal. 2001, 343, 171.
3. (b) Benaglia, M.; Cinquini, M.; Cozzi, F.; Puglisi, A.; Celentano, G. Adv. Synth. Catal. 2002, 344, 533.
4. (c) Benaglia, M.; Cinquini, M.; Cozzi, F.; Puglisi, A.; Celentano, G. J. Mol. Catal. A 2003, 204, 157.
5. (d) Gu, L.; Wu, Y.; Zhang, Y.; Zhao, G. J. Mol. Catal. A 2007, 263, 186.
6. (e) Liu, Y.-X.; Sun, Y.-N.; Tan, H.-H.; Liu, W.; Tao, J.-C. Tetrahedron: Asymmetry 2007, 78, 2649.
7. (f) Liu, Y.-X.; Sun, Y.-N.; Tan, H.-H.; Tao, J.-C. Catal. Lett. 2008, 120, 281.
8. (g) Font, D.; Jimeno, C.; Pericas, M. A. Org. Lett. 2006, 8, 4653.
9. (h) Kehat, T.; Portnoy, M. Chem. Commun. 2007, 2823.
10. (i) Giacalone, F.; Gruttadauria, M.; Marculescu, A. M.; Noto, R. Tetrahedron Lett. 2007, 48, 255.
11. (j) Gruttadauria, M.; Giacalone, F.; Marculescu, A. M.; Meo, P. L.; Riela, S.; Noto, R. Eur. J. Org. Chem. 2007, 4688.
12. (k) Font, D.; Sayalero, S.; Bastero, A.; Jimeno, C.; Pericás, M. A. Org. Lett. 2007, 9, 1943.
13. (l) Alsa, E.; Cambeiro, X. C.; Jimeno, C.; Pericás, M. A. Org. Lett. 2007, 9, 3717.
14. (m) Font, D.; Sayalero, S.; Bastero, A.; Jimeno, C.; Pericás, M. A. Org. Lett. 2008, 10, 337.
15. For reviews, see:
16. (a) Gruttadauria, M.; Giacalone, F.; Noto, R. Chem. Soc. Rev. 2008, 37, 1666.
17. (b) Gruttadauria, M.; Giacalone, F.; Noto, R. Adv. Synth. Catal. 2009, 351, 33.
18. (c) Trindade, A. F.; Gois, P. M. P.; Afonso, C. A. M. Chem. Rev. 2009, 109, 418. For a recent comprehensive review of polymeric immobilization in general, see:
19. (d) Lu, J.; Toy, P. H. Chem. Rev. 2009, 109, 815.
20. Gruttadauria, M.; Giacalone, F.; Marculescu, A. M.; Noto, R. Adv. Synth. Catal. 2008, 350, 1397.
21. (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
22. (b) Merrifield, R. B. Science 1965, 150, 178.
23. Kristensen, T. E.; Hansen, F. K.; Hansen, T. Eur. J. Org. Chem. 2009, 387.
24. van Esch, J.; Schoonbeek, F.; de Loos, M.; Kooijman, H.; Spek, A. L.; Kellogg, R. M.; Feringa, B. L. Chem.-Eur. J. 1999, 5, 937.
25. Moad, G.; Solomon, D. H. The Chemistry of Radical Polymerization, 2nd ed.; Elsevier: Amsterdam, Boston, 2006.
26. Dondoni, A. Angew. Chem., Int. Ed. 2008, 47, 8995.
27. For a thorough distinction between suspension, emulsion and dispersion polymerization, see: Arshady, R. Colloid Polym. Sci. 1992, 270, 717.
28. For a review of polymer microspheres by dispersion polymerization, see: Jayachandran, K. N. N.; Chatterji, P. R. J. Macromol. Sci. Polymer Rev. 2001, C41, 79.
29. Letsinger, R. L.; Kornet, M. J. J. Am. Chem. Soc. 1963, 85, 3045.
30. For an extensive discussion of loading issues of proline and prolineamides, see: Lombardo, M.; Easwar, S.; Pasi, F.; Trombini, C. Adv. Synth. Catal. 2009, 357, 276, and references therein.