CO-trapping reaction under thermolysis of alkoxyamines: Application to the synthesis of 3,4-cyclopenta-1-tetralones

Organic Letters

Volumn 7, Issue 14, 2005, Pages 2985-2988

  Uenoyama, Yoshitaka ^a   Tsukida, Masaaki ^a   Doi, Takashi ^a   Ryu, Ilhyong ^a   Studer, Armido ^b  

^a Osaka Prefecture University   (Japan)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 22244469456     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050951n     Document Type: Article

References (33)

1. For reviews on radical chemistry, see: (a) Renaud, P., Sibi, M. P., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2001; Vols. 1 and 2.
2. (b) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996.
3. (c) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic: London, 1992.
4. (a) Studer, A. Angew. Chem., Int. Ed. 2000, 39, 1108.
5. (b) Marque, S.; Fischer, H.; Baier, E.; Studer, A. J. Org. Chem. 2001, 66, 1146.
6. (c) Molawi, K.; Schulte, T.; Siegenthaler, K. O.; Wetter, C.; Studer, A. Chem. Eur. J. 2005, 11, 2335.
7. (d) Studer, A.; Schulte, T. Chem. Rec. 2005, 5, 27.
8. Studer, A. Chem. Soc. Rev. 2004, 33, 267.
9. Wetter, C.; Jantos, K.; Woithe, K.; Studer, A. Org. Lett. 2003, 5, 2899.
10. Wetter, C.; Studer, A. Chem. Commun. 2004, 174.
11. Teichert, A.; Jantos, K.; Harms, K.; Studer, A. Org. Lett. 2004, 6, 3477.
12. Herrera, A. J.; Studer, A. Synthesis 2005, 1389.
13. Allen, A. D.; Cheng, B.; Fenwick, M. H.; Givehchi, B.; Henry-Riyad, H.; Nikolaev, V. A.; Shikhova, E. A.; Tahmassebi, D.; Tidwell, T. T. Wang, S. J. Org. Chem. 2001, 66, 2611.
14. Allen, A. D.; Fenwick, M. F.; Henry-Riyad, H.; Tidwell T. T. J. Org. Chem. 2001, 66, 5759.
15. Leroi, C.; Fenet, B.; Couturier, J.-L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 1079.
16. Solomon, D. H.; Rizzardo, E.; Cacioli, P. US Patent 4,581,429; P. Eur. Pat. Appl. 135280; Chem. Abstr. 1985, 102, 221335q.
17. Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987.
18. Review: Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661.
19. (a) Daikh, B. E.; Finke, R. G. J. Am. Chem. Soc. 1992, 114, 2938.
20. (b) Fischer, H. J. Am. Chem. Soc. 1986, 108, 3925.
21. (c) Kothe, T.; Marque, S.; Martschke, R.; Popov, M.; Fischer, H. J. Chem. Soc., Perkin Trans. 2 1998, 1553.
22. Review: Fischer, H. Chem. Rev. 2001, 101, 3581.
23. For reviews on radical carbonylations, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
24. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
25. (c) Ryu, I. Chem. Soc. Rev. 2001, 30, 16.
26. Also see a review on acyl radicals: (d) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
27. (a) Wellington, K. D.; Cambie, R. C.; Rutledge, P. S.; Bergquist, P. R. J. Nat. Prod. 2000, 63, 79.
28. (b) Nicolaou, K. C.; Gray, J.; Tae, J. Angew. Chem., Int. Ed. 2001, 40, 3675.
29. (c) Nicolaou, K. C.; Gray, J.; Tae, J. Angew. Chem., Int. Ed. 2001, 40, 3679.
30. (d) Clive, D. L. J.; Wang, J. Angew. Chem., Int. Ed. 2003, 42, 3406.
31. Otera, J.; Orita, A. Jpn. Kokai Tokkyo Koho 2000, 2000-351741.
32. The acid may be formed from the corresponding tert-butyl ester via thermal fragmentation. The tert-butyl ester can be formed from acyl-TEMPO 3a via thermal ketene formation and subsequent trapping of the ketene with t-BuOH.
33. The unusual trans selectivity for the radical 5-exo cyclization was previously observed for similar PRE-mediated alkoxyamine isomerizations, see ref 2a. This is probably due to the reversibility of the 5-exo cyclization; see: Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6064.