Synthesis and application of phosphorus dendrimer immobilized azabis(oxazolines)

Organic Letters

Volumn 9, Issue 15, 2007, Pages 2895-2898

  Gissibl, Anja ^a,b   Padié, Clément ^a,b   Hager, Markus ^a,b   Jaroschik, Florian ^a,b   Rasappan, Ramesh ^a   Cuevas Yañez, Erick ^a   Turrin, Cédric Olivier ^b   Caminade, Anne Marie ^b   Majorai, Jean Pierre ^b   Reiser, Oliver ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547161292     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071128p     Document Type: Article

References (32)

1. Pfaltz, A. Acc Chem. Res. 1993, 26, 339.
2. (a) Lowenthal, R.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
3. (b) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726.
4. (c) Corey, E. J.; Imai, N.; Zhang, H. Y. J. Am. Chem. Soc. 1991, 113, 728. For recent reviews see:
5. (d) McManus, H. A.; Guiry, P. J. Chem. Rev. 2004, 104, 4151.
6. (e) Desimoni, G.; Faita, G.; Jorgensen, K. A. Chem. Rev. 2006, 106, 3561.
7. Rechavi, D.; Lemaire, M. Chem. Rev. 2002, 102, 3467.
8. (a) Glos, M.; Reiser, O. Org. Lett. 2000, 2, 2045.
9. (b) Werner, H.; Vicha, R.; Gissibl, A.; Reiser, O. J. Org. Chem. 2003, 68, 10166.
10. (c) Gissibl, A.; Finn, M. G.; Reiser, O. Org. Lett. 2005, 7, 2325.
11. (d) Werner, H.; Herrerias, C. I.; Glos, M.; Gissibl, A.; Fraile, J. M.; Perez, I.; Mayoral, J. A.; Reiser, O. Adv. Synth. Catal. 2006, 348, 125.
12. (a) Fraile, J. M.: Garcia, J. I.; Harmer, M. A.; Herrerias, C. I.; Mayoral, J. A.; Reiser, O.; Werner, H. J. Mater. Chem. 2002, 12, 3290.
13. (b) Fraile, J. M.; García, J. I.; Herrerías, C. I.; Mayoral, A.; Reiser, O.; Socuéllamos, A.; Werner, H. Chem.-Eur. J. 2004, 10, 2997.
14. (c) Fraile, J. M.; Garcia, J. I.; Herrerias, C. I.; Mayoral, J. A.; Reiser, O.; Vaultier, M. Tetrahedron Lett. 2004, 45, 6765.
15. (a) Caminade, A.-M.; Majorai, J.-P. Acc Chem. Res. 2004, 37, 341.
16. (b) Launay. N.; Caminade, A.-M.; Majoral, J.-P. J. Organomet. Chem. 1997, 529, 51.
17. Achiral dendritic bis(oxazoline)copper(II) catalysts have been reported: Chow, H.-F.; Mak, C C J. Org. Chem. 1997, 62, 5116.
18. (a) Tornøe, C W.; Meldal, M. In American Peptide Symposium; Lebl, M., Houghten, R. A., Eds.; American Peptide Society and Kluwer Academic Publishers: San Diego, CA, 2001, p 263.
19. (b) Tornøe, C W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
20. (c) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
21. (d) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192.
22. (e) Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128.
23. Huisgen, R. Pure Appl. Chem. 1989, 61, 613.
24. Synthesis of functional dendrimers using click chemistry: (a) Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2004, 43, 3928.
25. (b) Wu, P.; Malkoch, M.; Hunt, J. N.; Vestberg, R.; Kaltgrad, E.; Finn, M. G.; Fokin, V. V.; Sharpless, K. B.; Hawker, C. J. Chem. Commun. 2005, 5775.
26. (c) Kehat, T.; Portnoy, M. Chem. Commun., published online 2007, http://dx.doi.org./10.1039/b703016a).
27. (a) Gheorghe, A.; Matsuno, A.; Reiser, O. Adv. Synth. Catal. 2006, 348, 1016.
28. (b) Gheorghe, A.; Cuevas-Yanez, E.; Horn, J.; Bannwarth, W.; Narsaiah, B.; Reiser, O. Synlett 2006, 2767.
29. Löber, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Org. Lett. 2003, 5, 1753.
30. Matsumura, Y.; Maki, T.; Murakami. S.; Onomura, O. J. Am. Chem. Soc. 2003, 125, 2052.
31. (a) Rasappan, R.; Hager, M.; Gissibl, A.; Reiser, O. Org. Lett. 2006, 8, 6099.
32. (b) For a related observation on the addition of zincorganyls to aldehydes see: Bastero, A.; Font, D.; Pericas, M. A. J. Org. Chem. 2007, 72, 2460.