Gold- and silver-mediated cycloisomerizations of N-propargylamides

Organic Letters

Volumn 10, Issue 19, 2008, Pages 4379-4382

  Verniest, Guido ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349134050     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801847j     Document Type: Article

References (71)

1. Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
2. (a) Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395.
3. (b) Hamilton, G. L.; Rang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496.
4. Jimenez-Nunez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
5. Hoffman-Roder, A.; Krause, N. Org. Biomol. Chem. 2005, 3, 387.
6. For examples, see: (a) Davies, P. W.; Albrecht, S. J.-C. Chem. Commun. 2008, 238.
7. (b) Hashmi, A. S. K.; Salathé, R.; Frey, W. Eur. J. Org. Chem. 2007, 1648.
8. (c) Akana, J. A.; Bhattacharyya, K. X.; Müller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2007, 129, 7736.
9. (d) Ferrer, C.; Amijs, C. H. M.; Echavarren, A. M. Chem. - Eur. J. 2007, 13, 1358.
10. (e) Lavallo, V.; Frey, G. D.; Kousar, S.; Donnadieu, B.; Betrand, G. Proced. Natl Acad. Sci. U.S.A. 2007, 104, 13569.
11. (f) Luo, Y.; Li, Z.; Li, C.-J. Org. Lett. 2005, 7, 2675.
12. (g) Nevado, C.; Echavarren, A. M. Synthesis 2005, 2, 167.
13. (h) Mizushima, E.; Hayashi, T.; Tanaka, M. Org. Lett. 2003, 5, 3349.
14. (i) Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415.
15. (j) Fukada, Y.; Utimoto, K. J. Org. Chem. 1991, 56, 3729.
16. For examples, see: (a) Nieto-Oberhuber, C.; Perez-Galan, P.; Herrero-Gomez, E.; Lauterbach, T.; Rodriguez, C.; Lopez, S.; Hour, C.; Rosellon, A.; Cardenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2008, 130, 269.
17. (b) Hashmi, A. S. K.; Kurpejovic, E.; Wölfle, M.; Frey, W.; Bats. J. W. Adv. Synth. Catal. 2007, 349, 1743.
18. (c) Dai, L.-Z.; Qi, M.-J.; Shi, Y.-L.; Liu, X.-G.; Shi, M. Org. Lett. 2007, 9, 3191.
19. (d) Witham, C. A.; Mauleon, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
20. (e) Ferrer, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 1105.
21. (f) Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804.
22. (g) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962.
23. (a) Kirsch, S. F.; Binder, J. T.; Liebert, C.; Menz, H. Angew. Chem., Int. Ed. 2006, 45, 5878.
24. (b) Zhang, J.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2006, 45, 6704.
25. (c) Liu, Y.; Liu, M.; Guo, S.; Tu, H.; Zhou, Y.; Gao, H. Org. Lett. 2006, 8, 3445.
26. (d) Yao, T.; Zhang, X.; Larock, R. C. J. Org. Chem. 2005, 70, 7679.
27. (e) Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500.
28. (f) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285.
29. (a) Sato, K.; Menggenbateer; Kubota, T.; Asao, N. Tetrahedron 2008, 64, 787.
30. (b) Dyker, G.; Hildebrandt, D. J. Org. Chem. 2005, 70, 6093.
31. (c) Sato, K.; Asao, N.; Yamamoto, Y. J. Org. Chem. 2005, 70, 8977.
32. (d) Kim, N.; Kim, Y.; Park, W.; Sung, D.; Gupta, A. K.; Oh, C. H. Org. Lett. 2005, 7, 5289.
33. (e) Zhu, J.; Germain, A. R.; Porco, J. A. Angew. Chem., Int. Ed. 2004, 43, 1239.
34. (f) Asao, N.; Nogami, T.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 10921.
35. (g) Dyker, G.; Hildebrandt, D.; Liu, J.; Merz. K. Angew. Chem., Int. Ed. 2003, 42, 4399.
36. (h) Asao, N.; Takahashi, K.; Lee, S.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650.
37. (a) Rautenstrauch, V. J. Org. Chem. 1984, 49, 950.
38. (b) Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802.
39. (c) Correa, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Angew. Chem., Int. Ed. 2008, 47, 718.
40. (d) Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750.
41. (e) Yu, M.; Zhang, G.; Zhang. L. Org. Lett. 2007, 9, 2147.
42. (f) Luo, T.; Schreiber, S. L. Angew. Chem., Int. Ed. 2007, 46, 1.
43. (g) Faza, O. N.; Lopez, C. S.; Alvarez, R.; de Lera, A. R. J. Am. Chem. Soc. 2006, 128, 2434.
44. (h) Fürstner, A.; Hannen, P. Chem.-Eur. J. 2006, 12, 3006.
45. (i) Marion, N.; de Fremont, P.; Lemiere, G.; Stevens, E. D.; Fensterbank, L.; Malacria, M.; Nolan, S. P. Chem. Commun. 2006, 2048.
46. (j) Park, S.; Lee, D. J. Am. Chem. Soc. 2006, 128, 10664.
47. (k) Binder, J. T.; Kirsch, S. F. Org. Lett. 2006, 8, 2151.
48. (a) Buzas, A.; Gagosz, F. Org. Lett. 2006, 8, 515.
49. (b) Robles-Machin, R.; Adrio, J.; Carretero, J. C. J. Org. Chem. 2006, 71. 5023.
50. (c) Ritter, S.; Horino, Y.; Lex, J.; Schmalz, H.-G. Synlett 2006, 3309.
51. (a) Hashmi, A. S. K.; Weyrauch, J. P.; Frey, W.; Bats, J. W. Org. Lett. 2004, 6, 4391.
52. (b) Milton, M. D.; Inada, Y.; Nishibayashi, Y.; Uemura. S. Chem. Commun. 2004, 2712.
53. (a) Yamamoto, Y. J. Org. Chem. 2007, 72, 7817.
54. (b) Godet, T.; Vaxelaire, C.; Michel, C.; Milet, A.; Belmont, P. Chem. Eur. J. 2007, 13, 5632. and cited references. For examples of the use of Pt in alkyne activation, see:
55. (c) Dieguez-Vazquez, A.; Tzschucke, C. C.; Lam, W. Y.; Ley, S. V. Angew. Chem., Int. Ed. 2008, 47, 209.
56. (d) Kusama, H.; Ishida, K.; Funami, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2008, 47, 4903.
57. (e) Pujanauski, B. G.; Bhanu Prasad, B. A.; Sarpong, R. J. Am. Chem. Soc. 2006, 128, 6786.
58. (a) Deng, C.-L.; Song, R.-J.; Guo, S.-M.; Wang, Z.-Q.; Li, J.-H. Org. Lett. 2007, 9, 5111.
59. (b) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
60. (c) Stäben, S. T.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350.
61. (d) Mezailles, N.; Ricard, L.; Gagosz, F. Org. Lett. 2005, 7, 4133.
62. (e) Atsuko, O.; Hideto, I.; Masaya, S. J. Am. Chem. Soc. 2006, 128, 16486.
63. (f) Pan, J.-H.; Yang, M.; Gao, Q.; Zhu, N.-Y.; Yang, D. Synthesis 2007, 2539.
64. Garanti, L.; Sala, A.; Zecchi, G. Synthesis 1975, 10, 666.
65. Padwa, A.; Kinder, F. R. J. Org. Chem. 1993, 58, 21.
66. Mottet, C.; Hamelin, O.; Garavel, G.; Depres, J.-P.; Greene, A. E. J. Org. Chem. 1999, 64, 1380.
67. England, D.; Padwa, A. Org. Lett. 2008, 10, 3631.
68. (a) Maertens, F.; Van den Bogaert, A.; Compernolle, F.; Hoornaert, G. J. Eur. J. Org. Chem. 2004, 22, 4648.
69. (b) Philips, R. S.; Cohen, L. A. J. Am. Chem. Soc. 1986, 108, 2023.
70. Although the formation of 29 proceeds in low yield, the acid-catalyzed reaction is of interest because it suggests, that in certain circumstances, an acid source can be a better catalyst than gold for alkyne activation.
71. Rosenfeld, D. C.; Shekhar, S.; Takemiya, A.; Utsunomiya, M.; Hartwig, J. F. Org. Lett. 2006, 8, 4179.