A facile and efficient multi-gram synthesis of N-protected 5-(guanidinocarbonyl)-1H-pyrrole-2-carboxylic acids

European Journal of Organic Chemistry

Volumn , Issue 2, 2008, Pages 324-329

  Schmuck, Carsten ^a   Bickert, Volker ^a   Merschky, Michael ^a   Geiger, Lars ^a   Rupprecht, Daniel ^a   Dudaczek, Jürgen ^a   Wich, Peter ^a   Rehm, Thomas ^a   Machon, Uwe ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Anion receptors; Guanidinum cations; Protecting groups; Pyrroles

Indexed keywords

EID: 38349159880     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700756     Document Type: Article

References (26)

1. C. L. Hannon, E. V. Anslyn, Bioorg. Chem. Frontiers 1993, 3, 193-255.
2. a) G. V. Oshovsky, D. N. Reinhoudt, W. Verboom, Angew. Chem. 2007, 119, 2418-2445;
3. Angew. Chem. Int. Ed. 2007, 46, 2366-2393;
4. b) S. Kubik, C. Reyheller, S. J. Stuewe, J. Inclusion Phenom. Macrocyclic Chem. 2005, 52, 137-187.
5. For recent reviews on anion binding by artificial receptors including modified guanidinium cations see: a) P. Blondeau, M. Segura, R. Perez-Fernandez, J. de Mendoza, Chem. Soc. Rev. 2007, 36, 198-210;
6. b) K. A. Schug, W. Lindner, Chem. Rev. 2005, 105, 67-113;
7. c) M. D. Best, S. L. Tobey, E. V. Anslyn, Coord. Chem. Rev. 2003, 240, 3-15;
8. d) P. A. Gale, Coord. Chem. Rev. 2003, 240, 191-221;
9. e) R. J. Fitzmaurice, G. M. Kyne, D. Douheret, J. D. Kilburn, J. Chem. Soc. Perkin Trans. 1 2002, 841-864.
10. a) C. Schmuck, Coord. Chem. Rev. 2006, 250, 3053-3067;
11. b) C. Schmuck, L. Geiger, Curr. Org. Chem. 2003, 7, 1485-1502;
12. c) C. Schmuck, Chem. Eur. J. 2000, 6, 709-718.
13. Some examples: a) C. Schmuck, M. Heller, Org. Biomol. Chem. 2007, 5, 787-791;
14. b) C. Schmuck, D. Rupprecht, W. Wienand, Chem. Eur. J. 2006, 12, 9186-9195;
15. c) C. Schmuck, L. Geiger, J. Am. Chem. Soc. 2005, 127, 10486-10487.
16. a) C. Schmuck, T. Rehm, K. Klein, F. Gröhn, Angew. Chem. 2007, 119, 1723-1727;
17. Angew. Chem. Int. Ed. 2007, 46, 1693-1697;
18. b) C. Schmuck, T. Rehm, L. Geiger, M. Schäfer, J. Org. Chem. 2007, 72, 6162-6170;
19. c) C. Schmuck, T. Rehm, F. Gröhn, K. Klein, F. Reinhold, J. Am. Chem. Soc. 2006, 128, 1431-1431.
20. C. Schmuck, Eur. J. Org. Chem. 1999, 2397-2403.
21. J. W. Harbuck, H. Rapoport, J. Org. Chem. 1972, 37, 3618-3621.
22. W. F. Huffman, R. F. Hall, J. A. Grant, K. G. Holden, J. Med. Chem. 1978, 21, 413-415.
23. K. C. Nicolaou, A. A. Estrada, M. Zak, S. H. Lee, B. S. Safina, Angew. Chem. 2005, 117, 1402-1406;
24. Angew. Chem. Int. Ed. 2005, 44, 1378-1382.
25. L. Noss, P. A. Liddell, A. L. Moore, T. A. Moore, D. Gust, J. Phys. Chem. B 1997, 101, 458-465.
26. M. Goodman, M. Tomioka, C. J. Creighton, C. W. Zapf, Org. Lett. 2001, 3, 1133-1136.