Erratum: Direct synthesis of 2-(aminomethyl)-indoles through copper(I)-catalyzed domino three-component coupling and cyclization reactions (Angewandte Chemie - International Edition (2007) 46, (2295-2298) DOI: 10.1002/anie.200604342);Direct synthesis of 2-(aminomethyl)indoles through copper(I)-catalyzed domino three-component coupling and cyclization reactions

Angewandte Chemie - International Edition

Volumn 46, Issue 13, 2007, Pages 2295-2298

  Ohno, Hiroaki ^a   Ohta, Yusuke ^a   Oishi, Shinya ^a   Fujii, Nobutaka ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Cyclization; Domino reactions; Homogeneous catalysis; Indoles; Multicomponent reactions

Indexed keywords

CATALYST ACTIVITY; CHEMICAL BONDS; CYCLIZATION; NITROGEN COMPOUNDS; ORGANOMETALLICS;

C-C BOND; INDOLE DERIVATIVES; POLYCYCLIC INDOLES;

AROMATIC COMPOUNDS;

COPPER; INDOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

COPPER; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE;

EID: 34250351331     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200790078     Document Type: Erratum

References (38)

1. For recent reviews, see: a) G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875-2911;
2. b) S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920.
3. For recent examples, see: a) J. A. Morón, M. Campillo, V. Perez, M. Unzeta, L. Pardo, J. Med. Chem. 2000, 43, 1684-1691;
4. b) G. Spadoni, C. Balsamini, G. Diamantini, A. Tontini, G. Tarzia, J. Med. Chem. 2001, 44, 2900-2912;
5. c) S. Rivara, M. Mor, C. Silva, V. Zuliani, F. Vacondio, G. Spadoni, A. Bedini, G. Tarzia, V. Lucini, M. Pannacci, F. Fraschini, P. V. Plazzi, J. Med. Chem. 2003, 46, 1429-1439;
6. d) A. O. Stewart, M. D. Cowart, R. B. Moreland, S. P. Latshaw, M. A. Matulenko, P. A. Bhatia, X. Wang, J. F. Daanen, S. L. Nelson, M. A. Terranova, M. T. Namovic, D. L. Donnelly-Roberts, L. N. Miller, M. Nakane, J. P. Sullivan, J. D. Brioni, J. Med. Chem. 2004, 47, 2348-2355;
7. e) S. Rivara, S. Lorenzi, M. Mor, P. V. Plazzi, G. Spadoni, A. Bedini, G. Tarzia, J. Med. Chem. 2005, 48, 4049-4060;
8. f) M. Brands, J.-K. Ergüden, K. Hashimoto, D. Heimbach, C. Schröder, S. Siegel, J.-P. Stasch, S. Weigand, Bioorg. Med. Chem. Lett. 2005, 15, 4201-4205.
9. a) A. Kessler, H. Faure, C. Petrel, M. Ruat, P. Dauban, R. J. Dodd, Bioorg. Med. Chem. Lett. 2004, 14, 3345-3349;
10. b) C. Petrel, A. Kessler, P. Dauban, R. H. Dodd, D. Rognan, M. Ruat, J. Biol. Chem. 2004, 279, 18990-18997;
11. c) K. Ray, J. Tisdale, R. H. Dodd, P. Dauban, M. Ruat, J. K. Northup, J. Biol. Chem. 2005, 280, 37013-37020.
12. For recent synthesis of 2-(aminomethyl)indoles by other approaches, see: a) I. Ambrogio, S. Cacchi, G. Fabrizi, Org. Lett. 2006, 8, 2083-2086;
13. b) M. S. C. Pedras, M. Suchy, P. W. K. Ahiahonu, Org. Biomol. Chem. 2006, 4, 691-701.
14. B. M. Trost, Acc. Chem. Res. 2002, 35, 695-705.
15. a) H. Ohno, K. Miyamura, Y. Takeoka, T. Tanaka, Angew. Chem. 2003, 115, 2751-2754;
16. Angew. Chem. Int. Ed. 2003, 42, 2647-2650;
17. b) H. Ohno, K. Miyamura, T. Mizutani, Y. Kadoh, Y. Takeoka, H. Hamaguchi, T. Tanaka, Chem. Eur. J. 2005, 11, 3728-3741;
18. c) H. Ohno, T. Mizutani, Y. Kadoh, K. Miyamura, T. Tanaka, Angew. Chem. 2005, 117, 5243-5245;
19. Angew. Chem. Int. Ed. 2005, 44, 5113-5115;
20. d) H. Ohno, Y. Kadoh, N. Fujii, T. Tanaka, Org. Lett. 2006, 8, 947-950.
21. For recent reviews, see: a) H. Ohno, Chem. Pharm. Bull. 2005, 53, 1211-1226;
22. b) H. Ohno, Yakugaku Zasshi 2005, 125, 899-925.
23. S. Searles, Y. Li, B. Nassim, M.-T. R. Lopes, P. T. Tran, P. Crabbé, J. Chem. Soc. Perkin Trans. 1 1984, 747-751.
24. a) L. Ackermann, Org. Lett. 2005, 7, 439-442;
25. b) L. T. Kaspar, L. Ackermann, Tetrahedron 2005, 61, 11311-11316.
26. a) N. Olivi, P. Spruyt, J.-F. Peyrat, M. Alami, J.-D. Brion, Tetrahedron Lett. 2004, 45, 2607-2610;
27. b) B. Z. Lu, W. Zhao, H.-X. Wei, M. Dufour, V. Farina, C. H. Senanayake, Org. Lett. 2006, 8, 3271-3274.
28. For a two-component indole synthesis by a Sonogashira-type reaction, see: a) S. Cacchi, G. Fabrizi, L. M. Parisi, Org. Lett. 2003, 5, 3843-3846;
29. b) M. McLaughlin, M. Palucki, I. W. Davies, Org. Lett. 2006, 8, 3307-3310.
30. For biologically active polycyclic indoles with a 2-(amino-methyl)moiety, see: a) A. Espada, C. Jiménez, C. Debitus, R. Riguera, Tetrahedron Lett. 1993, 34, 7773-7776;
31. b) M. A. Rashid, K. R. Gustafson, M. R. Boyd, J. Nat. Prod. 2001, 64, 1454-1456;
32. c) R. A. Glennon, B. Grella, R. J. Tyacke, A. Lau, J. Westaway, A. L. Hudson, Bioorg. Med. Chem. Lett. 2004, 14, 999-1002;
33. d) C. Liu, M. N. Masuno, J. B. MacMillan, T. F. Molinski, Angew. Chem. 2004, 116, 6077-6080;
34. Angew. Chem. Int. Ed. 2004, 43, 5941-5945;
35. e) R. N. Sonnenschein, J. J. Farias, K. Tenney, S. L. Mooberry, E. Lobkovsky, J. Clardy, P. Crews, Org. Lett. 2004, 6, 779-782.
36. For recent synthesis of polycyclic indoles, see a) H. Kusama, J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2002, 124, 11592-11593;
37. b) M. Bandini, A. Melloni, F. Piccinelli, R. Sinisi, S. Tommasi, A. Umani-Ronchi, J. Am. Chem. Soc. 2006, 128, 1424-1425;
38. c) N. Kuroda, Y. Takahashi, K. Yoshinaga, C. Mukai, Org. Lett. 2006, 8, 1843-1845.