Photoinduced atom-transfer cyclization of α-iodocycloalkanones bearing an allenyl side chain

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3289-3292

  Lin, Hsien Hsun ^a   Chang, Wen Sheng ^a   Luo, Shun Yuan ^a   Sha, Chin Kang ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; HYDROGEN;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; IRRADIATION; LIGHT; REACTION ANALYSIS;

EID: 4644234207     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048822e     Document Type: Article

References (36)

1. (a) Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chem. Soc. 1986, 108, 2489.
2. (b) Curran, D. P.; Kim, D. Tetrahedron Lett. 1986, 27, 5821.
3. (c) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477.
4. (d) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140.
5. (e) Curran, D. P. Synthesis 1988, 417, 489.
6. (f) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
7. (g) Melikyan, G. G. Synthesis 1993, 833.
8. (h) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
9. (i) Snider, B. B. Chem. Rev. 1994, 96, 339.
10. (j) Curran, D. P.; Potter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996.
11. (k) Byers, J. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, Chapter 1.5.
12. (l) Gansauer, A.; Bluhm, H. Chem. Rev. 2000, 100, 2771.
13. (m) Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K. J. Org. Chem. 2001, 66, 7776.
14. (n) Li, C.; Wang, J. J. Org. Chem. 2002, 67, 1271.
15. (a) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1999, 40, 5511.
16. (b) Kim, S.; Song, H.-J.; Choi, T.-L.; Yoon, J.-Y. Angew. Chem., Int. Ed. 2001, 40, 2524.
17. (c) Ollivier, C.; Bark, T.; Renaud, P. Synthesis 2000, 1598.
18. (d) Kim, S.; Song, H.-J. Synlett 2002, 2110.
19. (e) Ouvry, G.; Zard, S. Z. Chem. Commun. 2003, 778.
20. (f) Vaillard, S. E.; Postigo, A.; Rossi, R. A. J. Org. Chem. 2004, 69, 2037.
21. (a) Sha, C.-K.; Jean, T.-S.; Wang, D.-C. Tetrahedron Lett. 1990, 31, 3745.
22. (b) Sha, C.-K.; Chiu, R.-T.; Yang, C.-F.; Yao, N.-T.; Tseng, W.-H.; Liao, F.-L.; Wang, S.-L. J. Am. Chem. Soc. 1997, 119, 4130.
23. (c) Sha, C.-K.; Santhosh, K. C.; Lih, S.-H. J. Org. Chem. 1998, 63, 2699.
24. (d) Sha, C.-K.; Ho, W.-Y. Chem. Commun. 1998, 2709.
25. (e) Sha, C.-K.; Lee, F.-K.; Chang, C.-J. J. Am. Chem. Soc. 1999, 121, 9875.
26. Sha, C.-K.; Santhosh, K. C.; Tseng, C.-T.; Lin, C.-T. Chem. Commun. 1998, 397.
27. For radical cyclization of allenes, see: (a) Crandall, J. K.; Ayers, T. A. Tetrahedron Lett. 1991, 32, 3659. (b) Macro-Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202. (c) Villar, F.; Renaud, P. Tetrahedron Lett. 1998, 39, 8655.
28. For radical cyclization of allenes, see: (a) Crandall, J. K.; Ayers, T. A. Tetrahedron Lett. 1991, 32, 3659. (b) Macro-Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202. (c) Villar, F.; Renaud, P. Tetrahedron Lett. 1998, 39, 8655.
29. For radical cyclization of allenes, see: (a) Crandall, J. K.; Ayers, T. A. Tetrahedron Lett. 1991, 32, 3659. (b) Macro-Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Grimaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202. (c) Villar, F.; Renaud, P. Tetrahedron Lett. 1998, 39, 8655.
30. Compound 1 was prepared from 5a using a sequence of reactions as shown in Scheme 2. 5-Iodo-1-pentyne was used as alkylating agent.
31. Preparation of 3a is shown in Scheme 2. The experimental procedures are in Supporting Information.
32. Johnson, E. P.; Chen, G.-P.; Fales, K. R.; Lenk, B. E.; Szendroi, R. J.; Wang, X.-J.; Carlson, J. A. J. Org. Chem. 1995, 60, 6595.
33. Sha, C.-K.; Young, J.-J.; Jean, T.-S. J. Org. Chem. 1987, 52, 3919.
34. Johnson, C. R.; Adems, J. P.; Branu, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskoković, M. R. Tetrahedron Lett. 1992, 33, 917.
35. Sha, C.-K.; Ho, W.-Y.; Mohanakrishnan, A. K.; Lin, C.-L.; Chu, SS.-Y. C. R. Acad. Sci., Ser. IIc: Chim. 2001, 4, 439.
36. Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 39, 1893.