Alkoxyamine-mediated radical cyclizations

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1079-1081

  Leroi, Corinne ^a   Fenet, Bernard ^b   Couturier, Jean Luc ^c   Guerret, Olivier ^c   Ciufolini, Marco A ^a  

^a UMR CNRS 5078   (France)

^b UNIVERSITÉ DE LYON   (France)

^c ARKEMA   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PHYSICAL CHEMISTRY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0141742136     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0341187     Document Type: Article

References (37)

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5. (a) Brace, N. O. J. Org. Chem. 1967, 32, 2711. Recent examples: (b) Barks, J. M.; Gilbert, B. C.; Parsons, A. F.; Upeandran, B. Tetrahedron Lett. 2001, 42, 3137. Related processes: (c) Miyabe, H.; Fujii, K.; Goto, T.; Naito, T. Org. Lett. 2000, 2, 4071. (d) Sibi, M. P.; Rhéault, T. R.; Miyabe, H. ; Patil, K.; Jasperse, C. P. C. R. Acad. Sci. Paris, Chem. 2001, 4, 581.
6. (a) Brace, N. O. J. Org. Chem. 1967, 32, 2711. Recent examples: (b) Barks, J. M.; Gilbert, B. C.; Parsons, A. F.; Upeandran, B. Tetrahedron Lett. 2001, 42, 3137. Related processes: (c) Miyabe, H.; Fujii, K.; Goto, T.; Naito, T. Org. Lett. 2000, 2, 4071. (d) Sibi, M. P.; Rhéault, T. R.; Miyabe, H. ; Patil, K.; Jasperse, C. P. C. R. Acad. Sci. Paris, Chem. 2001, 4, 581.
7. (a) Brace, N. O. J. Org. Chem. 1967, 32, 2711. Recent examples: (b) Barks, J. M.; Gilbert, B. C.; Parsons, A. F.; Upeandran, B. Tetrahedron Lett. 2001, 42, 3137. Related processes: (c) Miyabe, H.; Fujii, K.; Goto, T.; Naito, T. Org. Lett. 2000, 2, 4071. (d) Sibi, M. P.; Rhéault, T. R.; Miyabe, H. ; Patil, K.; Jasperse, C. P. C. R. Acad. Sci. Paris, Chem. 2001, 4, 581.
8. (a) Brace, N. O. J. Org. Chem. 1967, 32, 2711. Recent examples: (b) Barks, J. M.; Gilbert, B. C.; Parsons, A. F.; Upeandran, B. Tetrahedron Lett. 2001, 42, 3137. Related processes: (c) Miyabe, H.; Fujii, K.; Goto, T.; Naito, T. Org. Lett. 2000, 2, 4071. (d) Sibi, M. P.; Rhéault, T. R.; Miyabe, H. ; Patil, K.; Jasperse, C. P. C. R. Acad. Sci. Paris, Chem. 2001, 4, 581.
9. (a) Brace, N. O. J. Am. Chem. Soc. 1964, 86, 523. Recent examples: (b) Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 2002, 674. (c) Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Org. Chem. 2001, 66, 7776. (d) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041 and references therein. See also ref 6.
10. (a) Brace, N. O. J. Am. Chem. Soc. 1964, 86, 523. Recent examples: (b) Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 2002, 674. (c) Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Org. Chem. 2001, 66, 7776. (d) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041 and references therein. See also ref 6.
11. (a) Brace, N. O. J. Am. Chem. Soc. 1964, 86, 523. Recent examples: (b) Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 2002, 674. (c) Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Org. Chem. 2001, 66, 7776. (d) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041 and references therein. See also ref 6.
12. (a) Brace, N. O. J. Am. Chem. Soc. 1964, 86, 523. Recent examples: (b) Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 2002, 674. (c) Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Org. Chem. 2001, 66, 7776. (d) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041 and references therein. See also ref 6.
13. Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2002, 75, 853.
14. For example: disproportionation, recombination, etc.
15. For an example of disproportionation of nitroxyl radicals see: (a) Griller, D.; Perkins, M. J. J. Am. Chem. Soc. 1980, 102, 1354. For the reactivity of nitroxides see, for example: (b) Beckwith, A. L. J.; Bowry, V. W. ; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983. (c) Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992. (d) Aldabbagh, F.; Busfield, W. K.; Jenkins, I. D.; Thang, S. H. Tetrahedron Lett. 2000, 41, 3673.
16. For an example of disproportionation of nitroxyl radicals see: (a) Griller, D.; Perkins, M. J. J. Am. Chem. Soc. 1980, 102, 1354. For the reactivity of nitroxides see, for example: (b) Beckwith, A. L. J.; Bowry, V. W. ; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983. (c) Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992. (d) Aldabbagh, F.; Busfield, W. K.; Jenkins, I. D.; Thang, S. H. Tetrahedron Lett. 2000, 41, 3673.
17. For an example of disproportionation of nitroxyl radicals see: (a) Griller, D.; Perkins, M. J. J. Am. Chem. Soc. 1980, 102, 1354. For the reactivity of nitroxides see, for example: (b) Beckwith, A. L. J.; Bowry, V. W. ; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983. (c) Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992. (d) Aldabbagh, F.; Busfield, W. K.; Jenkins, I. D.; Thang, S. H. Tetrahedron Lett. 2000, 41, 3673
18. For an example of disproportionation of nitroxyl radicals see: (a) Griller, D.; Perkins, M. J. J. Am. Chem. Soc. 1980, 102, 1354. For the reactivity of nitroxides see, for example: (b) Beckwith, A. L. J.; Bowry, V. W. ; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4983. (c) Bowry, V. W.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 4992. (d) Aldabbagh, F.; Busfield, W. K.; Jenkins, I. D.; Thang, S. H. Tetrahedron Lett. 2000, 41, 3673
19. The precise dissociation temperature depends on the nature of R: (a) Le Mercier, C.; Lutz, J. F.; Marque, S.; Le Moigne, F.; Tordo, P.; Lacroix-Desmazes, P.; Boutevin, B.; Couturier, J. L.; Guerret, O.; Martschke, R.; Sobek, J.; Fischer, H. ACS Symp. Ser. 2000, 768, 108. (b) Marque, S.; Le Mercier, C.; Tordo, P.; Fischer, H. Macromolecules 2000, 33, 4403. (c) Goto, A. ; Kwak, Y.; Yoshikawa, C.; Tsujii, Y.; Sugiura, Y.; Fukuda, T. Macromolecules 2002, 35, 3520. See also ref 8.
20. The precise dissociation temperature depends on the nature of R: (a) Le Mercier, C.; Lutz, J. F.; Marque, S.; Le Moigne, F.; Tordo, P.; Lacroix-Desmazes, P.; Boutevin, B.; Couturier, J. L.; Guerret, O.; Martschke, R.; Sobek, J.; Fischer, H. ACS Symp. Ser. 2000, 768, 108. (b) Marque, S.; Le Mercier, C.; Tordo, P.; Fischer, H. Macromolecules 2000, 33, 4403. (c) Goto, A. ; Kwak, Y.; Yoshikawa, C.; Tsujii, Y.; Sugiura, Y.; Fukuda, T. Macromolecules 2002, 35, 3520. See also ref 8.
21. The precise dissociation temperature depends on the nature of R: (a) Le Mercier, C.; Lutz, J. F.; Marque, S.; Le Moigne, F.; Tordo, P.; Lacroix-Desmazes, P.; Boutevin, B.; Couturier, J. L.; Guerret, O.; Martschke, R.; Sobek, J.; Fischer, H. ACS Symp. Ser. 2000, 768, 108. (b) Marque, S.; Le Mercier, C.; Tordo, P.; Fischer, H. Macromolecules 2000, 33, 4403. (c) Goto, A. ; Kwak, Y.; Yoshikawa, C.; Tsujii, Y.; Sugiura, Y.; Fukuda, T. Macromolecules 2002, 35, 3520. See also ref 8.
22. Le Mercier, C. Dissertation, University of Provence, Aix-Marseille I, France, 2000.
23. 5: (a) Fischer, H.; Schuh, H. Int. J. Chem. Kinet. 1976, 8, 341. (b) Fischer, H.; Schuh, H. Helv. Chim. Acta 1978, 61, 7, 2463. (c) Fischer, H.; Munger, K. Int. J. Chem. Kinet. 1985, 17, 809. (d) Fischer, H.; Rubin, H. Helv. Chim. Acta 1996, 79, 1670.
24. 5: (a) Fischer, H.; Schuh, H. Int. J. Chem. Kinet. 1976, 8, 341. (b) Fischer, H.; Schuh, H. Helv. Chim. Acta 1978, 61, 7, 2463. (c) Fischer, H.; Munger, K. Int. J. Chem. Kinet. 1985, 17, 809. (d) Fischer, H.; Rubin, H. Helv. Chim. Acta 1996, 79, 1670.
25. 5: (a) Fischer, H.; Schuh, H. Int. J. Chem. Kinet. 1976, 8, 341. (b) Fischer, H.; Schuh, H. Helv. Chim. Acta 1978, 61, 7, 2463. (c) Fischer, H.; Munger, K. Int. J. Chem. Kinet. 1985, 17, 809. (d) Fischer, H.; Rubin, H. Helv. Chim. Acta 1996, 79, 1670.
26. 5: (a) Fischer, H.; Schuh, H. Int. J. Chem. Kinet. 1976, 8, 341. (b) Fischer, H.; Schuh, H. Helv. Chim. Acta 1978, 61, 7, 2463. (c) Fischer, H.; Munger, K. Int. J. Chem. Kinet. 1985, 17, 809. (d) Fischer, H.; Rubin, H. Helv. Chim. Acta 1996, 79, 1670.
27. Cf.: Marque, S.; Fischer, H.; Baier, E.; Studer, A. J. Org. Chem. 2001, 66, 1146, as well as refs 1. Conduct of the reaction in nonpolar solvents such as toluene, as well as in the neat state, produced unsatisfactory results, while higher boiling tertiary alcohols, such as triethyl carbinol, provided the same results as tert-butyl alcohol. Polar aprotic solvents such as NMP were also satisfactory.
28. 2, hydrogenolysis, Zn/AcOH. Dissolving metal reduction gave ambiguous results.
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35. -1 at 25°C: (a) Wagner, P. J.; Sedon, J. S.; Lindstrom, M. J. J. Am. Chem. Soc. 1978, 100, 2579. (b) Serra, A. C.; M. Da Silva Correa, C. M.; Vieira, M. A. M. S. A.; Gomes, M. A. Tetrahedron 1990, 46, 3061. At the temperature of our experiments (120°C), the fragmentation may become so fast that the lifetime of intermediate 11 is too short to permit further cyclization. For an interesting synthetic application of this property see: (c) Mouriès, V.; Delouvrié, B.; Lacôte, E.; Fensterbank, L.; Malacria, M. Eur. J. Org. Chem. 2002, 1776.
36. -1 at 25°C: (a) Wagner, P. J.; Sedon, J. S.; Lindstrom, M. J. J. Am. Chem. Soc. 1978, 100, 2579. (b) Serra, A. C.; M. Da Silva Correa, C. M.; Vieira, M. A. M. S. A.; Gomes, M. A. Tetrahedron 1990, 46, 3061. At the temperature of our experiments (120°C), the fragmentation may become so fast that the lifetime of intermediate 11 is too short to permit further cyclization. For an interesting synthetic application of this property see: (c) Mouriès, V.; Delouvrié, B.; Lacôte, E.; Fensterbank, L.; Malacria, M. Eur. J. Org. Chem. 2002, 1776.
37. -1 at 25°C: (a) Wagner, P. J.; Sedon, J. S.; Lindstrom, M. J. J. Am. Chem. Soc. 1978, 100, 2579. (b) Serra, A. C.; M. Da Silva Correa, C. M.; Vieira, M. A. M. S. A.; Gomes, M. A. Tetrahedron 1990, 46, 3061. At the temperature of our experiments (120°C), the fragmentation may become so fast that the lifetime of intermediate 11 is too short to permit further cyclization. For an interesting synthetic application of this property see: (c) Mouriès, V.; Delouvrié, B.; Lacôte, E.; Fensterbank, L.; Malacria, M. Eur. J. Org. Chem. 2002, 1776.