Intermolecular tandem addition-cyclization of bromoallenes: A facile synthesis of methylenecyclopropyl carboxylates and polysubstituted furans

Organic Letters

Volumn 8, Issue 22, 2006, Pages 5061-5064

  Xu, Lubin ^a   Huang, Xian ^a,b   Zhong, Fangrui ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750909096     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061993u     Document Type: Article

References (41)

1. Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds; Wiley-Vch: Weinheim, 2004; Vol. 2.
2. For organocopper-mediated substitutions, see examples: (a) Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3059.
3. (b) Caporusso, A. M.; Polizzi, C.; Lardicci, L. Tetrahedron Lett. 1987, 28, 6073.
4. (c) D'Aniello, F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870.
5. (d) Chemla, F.; Bernard, N.; Normant, J. Eur. J. Org. Chem 1999, 2067.
6. (e) Conde, J. J.; Mendelson, W. Tetrahedron Lett. 2000, 41, 811.
7. (f) Caporusso, A. M.; Zampieri, A.; Aronica, L. A.; Banti, D. J. Org. Chem. 2006, 71, 1902.
8. For palladium-catalyzed cross-coupling reactions, see; (a) MLrkl, G.; Attenberger, P.; Kellner, J. Tetrahedron Lett. 1988, 29, 3651.
9. (b) Gillmann, T.; Hülsen, T.; Massa, W.; Wocadlo, S. Synlett 1995, 1257.
10. (c) Saalfrank, R. W.; Haubner, M.; Deutscher, C.; Bauer, W.; Clark, T. J. Org. Chem. 1999, 64, 6166.
11. For the formation of nucleophilic allenyl metal reagents, see: (a) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1997, 62, 8976.
12. (b) Ma, S.; Yu, S.; Yin, S. J. Org. Chem. 2003, 68, 8996.
13. For ring-forming reactions, see: (a) Ohno, H.; Hamaguchi, H.; Tanada, T. Org. Lett. 2001, 3, 2269.
14. (b) Ohno, H.; Ando, K.; Hamaguchi, H.; Takeoka, Y.; Tanaka, T. J. Am. Chem. Soc. 2002, 124, 15255.
15. (a) Ohno, H.; Hamaguchi, H.; Ohata, M.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 1749.
16. (b) Ohno, H.; Hamaguchi, H.; Ohata, M.; Kosaka, S.; Tanaka, T. Heterocycles 2003, 61, 65.
17. (c) Ohno, H.; Hamaguchi, H.; Ohata, M.; Kosaka, S.; Tanaka, T. J. Am. Chem. Soc. 2004, 126, 8744.
18. (d) Hamaguchi, H.; Kosaka, S.; Ohno, H.; Tanaka, T. Angew. Chem., Int. Ed. 2005, 44, 1513.
19. (a) Singleton, D. A.; Huval, C. C. J. Org. Chem. 1994, 59, 2020.
20. (b) Ma, S.; Zhang, J. Angew. Chem., Int. Ed. 2003, 42, 183.
21. (c) Ma, S.; Lu, L.; Zhang, J. J. Am. Chem. Soc. 2004, 126, 9645.
22. (d) Ma, S.; Lu, L. J. Org. Chem. 2005, 70, 7629.
23. (e) Ma, S.; Lu, L.; Chen, G. Org. Lett. 2006, 8, 835.
24. Yan, Z. H.; Kern, E. R.; Gullen, E.; Cheng, Y. C.; Drach, J. C.; Zemlicka, J. J. Med. Chem. 2005, 48, 91 and references cited therein.
25. Cheng, C. M.; Shimo, T.; Somekawa, K.; Baba, M. Tetrahedron 1998, 54, 2031.
26. For the preparation of bromoallenes, see: (a) Landor, S. R.; Patel, A. N.; Whiter, P. F.; Greaves, P. M. J. Chem. Soc. (C) 1966, 1223.
27. (b) Elsevier, C. J.; Vermeer, P.; Gedanken, A.; Runge, W. J. Org. Chem. 1985, 50, 364.
28. 2 = 0.951.
29. N2′ reaction about bromoallenes. See examples in refs 2 and 5.
30. Lipshutz, B. H. Chem. Rev, 1986, 86, 795.
31. Natural Products Chemistry; Nkanishi, K., Ed.; Kondasha: Tokyo, 1974.
32. Some new methods have been reported for the synthesis of densely polysubstituted furans recently. See examples: (a) Ma, S.; Li, L. Org. Lett. 2000, 2, 941.
33. (b) Stauffer, F.; Neier, R. Org. Lett. 2000, 2, 3535.
34. (c) Ma, S.; Zhang, J. Chem. Commun. 2000, 117.
35. (d) Nair, N.; Menon, R. S.; Vinod, A. U.; Viji, S. Tetrahedron Lett. 2002, 43, 2293.
36. (e) Nair, N.; Vinod, A. U.; Abhilash, N.; Menon, R. S.; Santhi, V.; Varma, R. L.; Viji, S.; Mathew, S.; Srinivas, R. Tetrahedron 2003, 59, 10279.
37. (f) Yavari, I.; Alizadeh, A.; Anary-Abbasinejad, M.; Bijanzadeh, H. R. Tetrahedron 2003, 59, 6083.
38. (g) Aurrecoechea, J. M.; Perez, E. Tetrahedron Lett. 2003, 44, 3263.
39. (h) Azizian, J.; Mohammadi, A. A.; Karimi, A. R. Heteroatom Chem. 2005, 16, 259.
40. (i) Ma, S.; Zhang, J. J. Am. Chem. Soc. 2003, 125, 12386.
41. (j) Zhou, C. Y.; Chan, P. W. H.; Che, C. M. Org. Lett. 2006, 8, 325.