New cyclization of 4-oxahepta-1,6-diynes bearing sulfur and selenium functional groups

Organic Letters

Volumn 12, Issue 18, 2010, Pages 4192-4194

  Yoshimatsu, Mitsuhiro ^a   Watanabe, Hiroyasu ^a   Koketsu, Eri ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; SELENIUM; SULFUR;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ISOMERISM;

CYCLIZATION; FURANS; ISOMERISM; MOLECULAR STRUCTURE; ORGANIC CHEMISTRY PROCESSES; SELENIUM; SULFUR;

EID: 77956600086     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101540s     Document Type: Article

References (35)

1. Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry II; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Oxford, 1997; Vol. 2, pp 395.
2. Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 4, pp 657.
3. Gung, B. W.; Dickson, H.; Shockley, S. Tetrahedron Lett. 2001, 42, 4761
4. Marshall, J. A.; Bartley, G. S. J. Org. Chem. 1994, 59, 7169
5. Marshall, J. M.; Yu, B. J. Org. Chem. 1994, 59, 324
6. Sromek, A. W.; Kelin, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2004, 43, 2280 Pd: Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816
7. Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1995, 34, 1581 Cu:
8. Kim, J. T.; Kelin, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2003, 42, 98
9. Kelin, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95 Au:
10. Hashmi, A. S. K.; Schwarz, L.; Choi, J.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285
11. Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553 Mn:
12. Melikyan, G. G.; Vostrowsky, O.; Bauer, W.; Bestmann, H. J.; Khan, M.; Nicholas, K. M. J. Org. Chem. 1994, 59, 222 Base:
13. MaGee, D. I.; Leach, J. D.; Mallais, T. C. Tetrahedron Lett. 1997, 38, 1289 P:
14. Jung, C.; Wang, J.; Krische, M. J. Am. Chem. Soc. 2004, 126, 4118
15. Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc. 1995, 117, 7255
16. Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687
17. Ma, S.; Zhang, J. Chem. Commun. 2000, 117
18. Marat, X.; Monteiro, N.; Balme, G. Synlett 1997, 845 Mg:
19. 2:
20. Silva, G. V. J.; Pelisson, M. M. M.; Constantino, M. G. Tetrahedron Lett. 1994, 35, 7327 Ag:
21. Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966
22. Marshall, J. A.; DuBay, W. J. J. Org. Chem. 1994, 59, 1703
23. Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110 Au: Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 6962 Mo: McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363 Hg: Marson, C. M.; Harper, S.; Wrigglesworth, R. J. Chem. Soc., Chem. Commun. 1994, 1879 Ru: Seiller, B.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1994, 493
24. Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 1999, 121, 11680 Rh: Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490 Base: Marshall, J. A.; DuBay, W. J. J. Org. Chem. 1993, 58, 3435 Thermal: Hayakawa, K.; Yodo, M.; Ohsuki, S.; Kanematsu, K. J. Am. Chem. Soc. 1984, 106, 6735
25. Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850
26. Hashmi, A. S. K.; Sinha, P. Adv. Synth. Catal. 2004, 346, 432
27. Modern Allene Chemistry; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 1, p 3.
28. Dihydrofuran from diyne: Pd
29. Wang, F.; Tong, X.; Cheng, J.; Zhang, Z. Chem. - Eur. J. 2004, 10, 5338 Rh: Tanaka, K.; Otake, Y.; Wada, A.; Noguchi, K.; Hirano, M. Org. Lett. 2007, 9, 2203
30. Bartlett, A. J.; Laird, T.; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315 Furan from enyne: Parsons, P. J.; Waters, A. J.; Walter, D. S.; Board, J. J. Org. Chem. 2007, 72, 1395 Hg: Barluenga, J.; Aznar, F.; Bayod, M. Tetrahedron Lett. 1988, 29, 5029 Base: Diels-Alder type: Kudoh, T.; Mori, T.; Shirahama, M.; Yamada, M.; Ishikawa, T.; Saito, S.; Kobayashi, H. J. Am. Chem. Soc. 2007, 129, 4939
31. Godoi, B.; Speranca, A.; Back, D. F.; Brandao, R.; Nogueira, C. W.; Zeni, G. J. Org. Chem. 2009, 74, 3469 and references therein
32. Yoshimatsu, M.; Naito, M.; Shimizu, H.; Muraoka, O.; Tanabe, G.; Kataoka, T. J. Org. Chem. 1996, 61, 8200
33. Yoshimatsu, M.; Machida, K.; Fuseya, T.; Shimizu, H.; Kataoka, T. J. Chem. Soc., Perkin Trans. 1 1996, 1839
34. Yoshimatsu, M.; Otani, T.; Matsuda, S.; Yamamoto, T.; Sawa, A. Org. Lett. 2008, 10, 4251
35. Yoshimatsu, M.; Yamamoto, T.; Sawa, A.; Kato, T.; Tanabe, G.; Muraoka, O. Org. Lett. 2009, 11, 2952