Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from N-(pent-2-en-4-ynyl)-β-lactams

Organic Letters

Volumn 10, Issue 22, 2008, Pages 5187-5190

  Peng, Yu ^a   Yu, Meng ^a   Zhang, Liming ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349162246     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802159v     Document Type: Article

References (27)

1. For selected recent reviews on Au catalysis, see: (a) Arcadi, A. Chem. Rev. 2008, 108, 3266-3325.
2. (b) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395-3442.
3. (c) Gorin, D. J.; Sherry, B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351-3378.
4. (d) Jimenez-Nunez, E.; Echavarren, A. M. Chem. Commun. 2007, 333-346.
5. (e) Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239-3265.
6. (f) Fürstner, A.; Davis, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410-3449.
7. (g) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180-3211.
8. (h) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271-2296.
9. Li, G.; Huang, X.; Zhang, L. Angew. Chem., Int. Ed. 2008, 47, 346-349.
10. Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 10546-10547.
11. (a) Coates, R. M.; Muskopf, J. W.; Senter, P. A. J. Org. Chem. 1985, 50, 3541-3557.
12. (b) Ruck-Braun, K.; Moller, C. Chem. Eur. J. 1999, 5, 1038-1044.
13. 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidenegold(I) bis(trifluoromethanesulfonyl)imide; for its first catalysis study, see: Li, G.; Zhang, L. Angew. Chem., Int. Ed. 2007, 46, 5156-5159.
14. For its synthesis, see: Ricard, L.; Gagosz, F. Organometallics 2007, 26, 4704-4707.
15. For related studies, see: (a) Hashmi, A. S. K.; Buehrle, M.; Salathe, R.; Bats, J. W. Adv. Synth. Catal. 2008, 350, 2059-2064.
16. (b) Istrate, F. M.; Gagosz, F. Org. Lett. 2007, 9, 3181-3184.
17. (c) Cariou, K.; Ronan, B.; Mignani, S.; Fensterbank, L.; Malacria, M. Angew. Chem., Int. Ed. 2007, 46, 1881-1884.
18. For selected previous total synthesis, see: (a) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688-4693.
19. (b) Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513-3518.
20. (c) Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W. K.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183-10194.
21. (d) Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445-1446.
22. (e) Guazzelli, G.; Lazzaroni, R.; Settambolo, R. Synthesis 2005, 3119-3123.
23. (f) Sun, Z.; Yu, S.; Ding, Z.; Ma, D. J. Am. Chem. Soc. 2007, 129, 9300-9301.
24. (g) Stead, D.; O'Brien, P.; Sanderson, A. Org. Lett. 2008, 10, 1409-1412.
25. (a) Daly, J. W. In Progress in the Chemistry of Organic Natural Products; Springer-Verlag: Vienna, 1982; Vol. 41, pp 205-340.
26. (b) Daly, J. W.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectiues; Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 4, pp 1-274.
27. 2.