Transition Metal-Catalyzed Radical Cyclizations: A Low-Temperature Process for the Cyclization of N-Protected N-Allyltrichloroacetamides to Trichlorinated γ-Lactams and Application to the Stereoselective Preparation of β,γ-Disubstituted γ-Lactams

Journal of Organic Chemistry

Volumn 58, Issue 2, 1993, Pages 464-470

  Nagashima, Hideo ^a   Ozaki, Nobuyasu ^a   Ishii, Masayuki ^a   Seki, Koji ^a   Washiyama, Masayoshi ^a   Itoh, Kenji ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000340186     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00054a034     Document Type: Article

References (34)

1. For recent reviews: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986.
2. Curran, D. P. Synthesis 1988, 417, 489.
3. Stork, G. Bull. Chem. Soc. Jpn. 1989, 28, 723.
4. Nagashima, H.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J. Tetrahedron Lett. 1983, 23, 2395.
5. Nagashima, H.; Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985.
6. Nagashima, H.; Wakamatsu, K.; Itoh, K. J. Chem. Soc., Chem. Commun. 1984, 652.
7. Nagashima, H.; Ara, K.; Wakamatsu, H.; Itoh, K. J. Chem. Soc., Chem. Commun. 1985, 518.
8. Nagashima, H.; Wakamatsu, H.; Ozaki, N.; Ishii, T.; Watanabe, M.; Tajima, T.; Itoh, K. J. Org. Chem. 1992, 57, 1682.
9. Cyclization of N-allyldichloroacetamides: Tseng, C. K.; Teach, E. G.; Simmons, R. W. Synth. Commun. 1984, 14, 1027.
10. Hayes, T. K.; Villani, R.; Weinreb, S. M. J. Am. Chem. Soc. 1988, 110, 5533.
11. Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671.
12. Phelps, J. C.; Bergbreiter, D. E.; Lee, G. M.; Villani, R.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 3915.
13. Lee, G. M.; Weinreb, S. M. J. Org. Chem. 1990, 55, 1281.
14. A part of these results has appeared in our preliminary account: Nagashima, H.; Ozaki, N.; Seki, K.; Ishii, M.; Itoh, K. J. Org. Chem. 1989, 54, 4497.
15. Hirai, Y.; Hagiwara, A.; Terada, T.; Yamazaki, T. Chem. Lett. 1987, 2417.
16. Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536.
17. Clough, J. M.; Pattenden, G.; Write, P. G. Tetrahedron Lett. 1989, 30, 7469.
18. Stork, G.; Man, P. Heterocycles 1989, 28, 723.
19. Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121.
20. Ishibashi, H.; So, S. T.; Okouchi, K.; Sato, T.; Nakamura, N.; Nakatani, H.; Ikeda, M. J. Org. Chem. 1991, 56, 95.
21. Padwa, A.; Nimmesgern, H.; Wong, G. S. K. J. Org. Chem. 1985, 50, 5620.
22. Ueno, Y.; Tanaka, C.; Okawara, M. Chem. Lett. 1983, 795.
23. Hart, D. J.; Tsai, Y.-M. J. Am. Chem. Soc. 1982, 104, 1430.
24. Danishefsky, S. J.; Panek, J. S. J. Am. Chem. Soc. 1987, 109, 917.
25. Spellmeyer, D. C.; Houk, K. J. Org. Chem. 1987, 52, 959.
26. Beckwith, A. L.; Schiesser, C. H. Tetrahedron 1985, 41, 3295.
27. Greene, T. W.; Wuts, P. G. Protective Groups in Organic Synthesis; John Willey and Sons: New York, 1991.
28. Wilson, F. G.; Wheeler, T. S. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. 1, p 102.
29. Trost, B. M.; Keinan, E. J. Org. Chem. 1979, 44, 3451.
30. Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
31. For a extensive review;Tsuji, J. Tetrahedron 1986, 42, 4361.
32. Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901.
33. Dillard, R. D.; Eaton, N. R. J. Org. Chem. 1966, 31, 122.
34. Collington, E. W.; Meyers, A. I. J. Org. Chem. 1971, 36, 3044.