The first preparation of β-lactones by radical cyclization

Organic Letters

Volumn 5, Issue 5, 2003, Pages 757-759

  Castle, Kerstin ^a   Hau, Chee San ^a   Sweeney, J B ^a   Tindall, Craig ^a,b  

^a UNIVERSITY OF READING   (United Kingdom)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CARBON; LACTONE DERIVATIVE; OXYGEN RADICAL; TOLUENE;

ARTICLE; CYCLIZATION; CYCLOADDITION; MOLECULAR STABILITY; PHOTODYNAMICS; QUANTUM YIELD; SYNTHESIS; THERMODYNAMICS; THERMOSTABILITY;

EID: 0037594253     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0340235     Document Type: Article

References (30)

1. For early reports of formation of cyclobutanes by 4-exo-trig cyclization, see: Piccardi, P.; Modena, M.; Cavalli, L. J. Chem. Soc. C 1971, 3959-3966. Piccardi, P.; Massardo, P.; Modena, M.; Santoro, E. J. Chem. Soc., Perkin Trans. 1 1971, 982-988.
2. For early reports of formation of cyclobutanes by 4-exo-trig cyclization, see: Piccardi, P.; Modena, M.; Cavalli, L. J. Chem. Soc. C 1971, 3959-3966. Piccardi, P.; Massardo, P.; Modena, M.; Santoro, E. J. Chem. Soc., Perkin Trans. 1 1971, 982-988.
3. Walling, C.; Pearson, M. S. J. Am. Chem. Soc. 1964, 86, 2262-2266. Walling, C.; Cooley, J. H.; Ponaras, A. A.; Racah, E. J. J. Am. Chem. Soc. 1966, 88, 5361-5363. Julia, M. Acc. Chem. Res. 1971, 386-392. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
4. Walling, C.; Pearson, M. S. J. Am. Chem. Soc. 1964, 86, 2262-2266. Walling, C.; Cooley, J. H.; Ponaras, A. A.; Racah, E. J. J. Am. Chem. Soc. 1966, 88, 5361-5363. Julia, M. Acc. Chem. Res. 1971, 386-392. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
5. Walling, C.; Pearson, M. S. J. Am. Chem. Soc. 1964, 86, 2262-2266. Walling, C.; Cooley, J. H.; Ponaras, A. A.; Racah, E. J. J. Am. Chem. Soc. 1966, 88, 5361-5363. Julia, M. Acc. Chem. Res. 1971, 386-392. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
6. Walling, C.; Pearson, M. S. J. Am. Chem. Soc. 1964, 86, 2262-2266. Walling, C.; Cooley, J. H.; Ponaras, A. A.; Racah, E. J. J. Am. Chem. Soc. 1966, 88, 5361-5363. Julia, M. Acc. Chem. Res. 1971, 386-392. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
7. Gill, G. B.; Pattenden, G.; Reynolds, S. J. Tetrahedron Lett. 1989, 30, 3229-3232. Pattenden, G.; Reynolds, S. J. Tetrahedron Lett. 1991, 32, 259-262. Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369-378. Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 379-385.
8. Gill, G. B.; Pattenden, G.; Reynolds, S. J. Tetrahedron Lett. 1989, 30, 3229-3232. Pattenden, G.; Reynolds, S. J. Tetrahedron Lett. 1991, 32, 259-262. Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369-378. Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 379-385.
9. Gill, G. B.; Pattenden, G.; Reynolds, S. J. Tetrahedron Lett. 1989, 30, 3229-3232. Pattenden, G.; Reynolds, S. J. Tetrahedron Lett. 1991, 32, 259-262. Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369-378. Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 379-385.
10. Gill, G. B.; Pattenden, G.; Reynolds, S. J. Tetrahedron Lett. 1989, 30, 3229-3232. Pattenden, G.; Reynolds, S. J. Tetrahedron Lett. 1991, 32, 259-262. Gill, G. B.; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 369-378. Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans. 1 1994, 379-385.
11. (a) Ishibashi, H.; Nakamura, N.; Sato, T.; Takenuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. Ishibashi, H.; Kameoka, C.; Yoshikawa, A.; Ueda, R.; Kodama, K.; Sato, T.; Ikeda, M. Synlett 1993, 649-650. Ishibashi, H.; Kameoka, C.; Sato, T.; Ikeda, M. Synlett 1994, 445-446.
12. (a) Ishibashi, H.; Nakamura, N.; Sato, T.; Takenuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. Ishibashi, H.; Kameoka, C.; Yoshikawa, A.; Ueda, R.; Kodama, K.; Sato, T.; Ikeda, M. Synlett 1993, 649-650. Ishibashi, H.; Kameoka, C.; Sato, T.; Ikeda, M. Synlett 1994, 445-446.
13. (a) Ishibashi, H.; Nakamura, N.; Sato, T.; Takenuchi, M.; Ikeda, M. Tetrahedron Lett. 1991, 32, 1725-1728. Ishibashi, H.; Kameoka, C.; Yoshikawa, A.; Ueda, R.; Kodama, K.; Sato, T.; Ikeda, M. Synlett 1993, 649-650. Ishibashi, H.; Kameoka, C.; Sato, T.; Ikeda, M. Synlett 1994, 445-446.
14. (b) Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276-1284. Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489-502.
15. (b) Ishibashi, H.; Kameoka, C.; Iriyama, H.; Kodama, K.; Sato, T.; Ikeda, M. J. Org. Chem. 1995, 60, 1276-1284. Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489-502.
16. (c) Fremont, S. L.; Belletire, J. L.; Ho, D. M. Tetrahedron Lett. 1991, 32, 2335-2338.
17. (d) D'Annibale, A.; Resta, S.; Trogolo, C. Tetrahedron Lett. 1995, 36, 9039-9042. D'Annibale, A.; Pesce, A.; Resta, S.; Trogolo, C. Tetrahedron 1997, 53, 13129-13138. D'Annibale, A.; Pesce, A.; Resta, S.; Trogolo, C. Tetrahedron Lett. 1997, 38, 1829-1832.
18. (d) D'Annibale, A.; Resta, S.; Trogolo, C. Tetrahedron Lett. 1995, 36, 9039-9042. D'Annibale, A.; Pesce, A.; Resta, S.; Trogolo, C. Tetrahedron 1997, 53, 13129-13138. D'Annibale, A.; Pesce, A.; Resta, S.; Trogolo, C. Tetrahedron Lett. 1997, 38, 1829-1832.
19. (d) D'Annibale, A.; Resta, S.; Trogolo, C. Tetrahedron Lett. 1995, 36, 9039-9042. D'Annibale, A.; Pesce, A.; Resta, S.; Trogolo, C. Tetrahedron 1997, 53, 13129-13138. D'Annibale, A.; Pesce, A.; Resta, S.; Trogolo, C. Tetrahedron Lett. 1997, 38, 1829-1832.
20. (e) Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron Lett. 1996, 37, 1397-1400. Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron 1998, 54, 1029-1040. Boiteau, L.; Boivin, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron 1998, 54, 2087-2098.
21. (e) Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron Lett. 1996, 37, 1397-1400. Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron 1998, 54, 1029-1040. Boiteau, L.; Boivin, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron 1998, 54, 2087-2098.
22. (e) Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron Lett. 1996, 37, 1397-1400. Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron 1998, 54, 1029-1040. Boiteau, L.; Boivin, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron 1998, 54, 2087-2098.
23. (a) Esker, J. L.; Newcomb, M. Tetrahedron Lett. 1993, 34, 6877-6880.
24. (b) Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1994, 35, 5629-5632. Boivin, J.; Callier-Dublanchet, A.-C.; Quiclet-Sire, B.; Schiano, A. ; Zard, S. Z. Tetrahedron 1995, 51, 6517-6528. Callier-Dublanchet, A.-C.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 8791-8794.
25. (b) Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1994, 35, 5629-5632. Boivin, J.; Callier-Dublanchet, A.-C.; Quiclet-Sire, B.; Schiano, A. ; Zard, S. Z. Tetrahedron 1995, 51, 6517-6528. Callier-Dublanchet, A.-C.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 8791-8794.
26. (b) Boivin, J.; Yousfi, M.; Zard, S. Z. Tetrahedron Lett. 1994, 35, 5629-5632. Boivin, J.; Callier-Dublanchet, A.-C.; Quiclet-Sire, B.; Schiano, A. ; Zard, S. Z. Tetrahedron 1995, 51, 6517-6528. Callier-Dublanchet, A.-C.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 8791-8794.
27. (c) Clark, A. J.; Peacock, J. L. Tetrahedron Lett. 1998, 39, 1265-1268.
28. Knochel, P.; Chou, T. S.; Jubert, C.; Rajagopal, D. J. Org. Chem. 1993, 58, 588.
29. Stereochemical assignment of β-lactones were made following the observations of Mulzer et al.: Mulzer, J.; Pointner, A.; Chucholowski, A.; Bruentrup, G. J. Chem. Soc., Chem. Commun. 1979, 52-54.
30. Barton, D. H. R.; Crich, D.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1983, 939-941.