Copper-catalyzed facile carbon-carbon bond forming reactions at the α- position of α,α,γ-trichlorinated γ-lactams

Tetrahedron

Volumn 55, Issue 6, 1999, Pages 1687-1706

  Iwamatsu, Sho ichi ^a   Kondo, Hideo ^b   Matsubara, Kouki ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

Addition; Catalysis; Copper; Lactam

Indexed keywords

COPPER; LACTAM;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033524651     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01198-3     Document Type: Article

References (39)

1. For reviews of transition metal-catalyzed radical reactions, see: (a) Iqbal, J.; Bhatia, B.; Nayyer, N. K. Chem. Rev. 1994, 94, 519.
2. (b) Kochi, J. K., Organometallic Mechanisms and Catalysts, Academic Press, New York 1978.
3. For reviews of atom transfer radical reactions, see: (a) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-586.
4. (b) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bands, Pergamon: New York, 1986.
5. (c) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reaction, VCH, Weinheim, 1996, 23-115.
6. (d) Curran, D. P. In Comprehensive Organic Synthesis (Eds. Trost, B. M.; Fleming, I.), Pergamon, Oxford, 1991, vol. 4, 715.
7. (a) Murai, S; Sonoda, N; Tsutumi, S. J. Org. Chem. 1964, 29, 2104.
8. (b) Tsuji, J.; Mori, Y. Tetrahedron 1972, 28, 29.
9. (c) Matsumoto, H.; Nikaido, T.; Nagai, Y. J. Org. Chem. 1976, 41, 396.
10. (d) Tsuji, J.; Sato, K.; Nagashima, H. Chem. Lett. 1981, 1169.
11. (a) Nagashima, H.; Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K., Tomo, Y.; Tsuji, I., J. Org. Chem. 1990, 55, 985.
12. (b) Takano, S.; Nishizawa, S.; Akiyama, M.; Ogasawara, K., Synthesis 1984, 949.
13. (a) Pirrung, F. O. H.; Hiemstra, H; Speckamp, W. N.; Kaptein, B.; Schoemaker, H. E., Synthesis 1995, 458.
14. (b) Pirrung, F. O. H.; Hiemstra, H; Speckamp, W. N.; Kaptein, B.; Schoemaker, H. E., Tetrahedron 1994, 50, 12415.
15. (c) Udding, J. H.; Hiemstra, H; Speckamp, W. N., J. Chem. Soc. Perkin Trans. 2. 1992, 1529.
16. (a) Nagashima, H.; Wakamatsu, H.; Ozaki, N.; Ishii, M., Seki, K.; Washiyama, M.; Itoh, K., J. Org. Chem. 1993, 58, 464.
17. (b) Nagashima, H.; Wakamatsu, H.; Ozaki, N.; Ishii, M., Watanabe, M.; Tajima, T.; Itoh, K., ibid. 1992, 57, 1682.
18. (c) Nagashima, H.; Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J., ibid. 1990, 55, 985.
19. (d) Nagashima, H.; Ozaki, N.; Seki, K.; Ishii, M.; Itoh, K., ibid. 1989, 54, 4497.
20. (a) Rachita, M. A.; Slough, G. A., Tetrahedron Lett. 1993, 34, 6821, 6825.
21. (b) Baldovini, N.; Bertrand, M.-P.; Carriere, A.; Nouguier, R., Plancher, J.-M., J. Org. Chem. 1996, 61, 3205.
22. (c) Benedetti, M., Forti, L.; Ghelfi, F.; Pagnoni, U. M.; Ronzoni, R., Tetrahedron 1997, 53, 14031.
23. (a) Lee, G. M.; Weinreb, S. M., J. Org. Chem. 1990, 55, 1281.
24. (b) Phelps, J. C.; Bergbreiter, D. E.; Lee, G. M.; Villani, R.; Weinreb, S. M., Tetrahedron Lett. 1989, 30, 3915.
25. (c) Lee, G. M.; Parvez, M.; Weinreb, S. M., Tetrahedron 1988, 44, 4671.
26. (d) Hayes, T. K.; Villani, R.; Weinreb, S. M., J. Am. Chem. Soc. 1988, 110, 5533.
27. (e) Hayes, T. K.; Freyer, A. J.; Parvez, M.; Weinreb, S. M., J. Org. Chem. 1986, 51, 5501.
28. (a) Ishibashi, H.; Uemura, N.; Nakatani, H.; Okazaki, M.; Sato, T.; Nakamura, N.; Ikeda, M., J. Org. Chem. 1993, 58, 2360.
29. (b) Ishibashi, H.; So, T. S.; Okochi, K.; Sato, T.; Nakamura, N.; Nakatani, H.; Ikeda, M., ibid. 1991, 56, 95.
30. (c) Seijas, J. A.; V-Tato, M. P.; Castedo, L.; Éstevez, R. J.; Ónega, M. G.; Ruíz, M., Tetrahedron 1992, 48, 1637.
31. (d) Hirai, Y.; Hagiwara, A.; Terada, T.; Yamazaki, T., Chem. Lett. 1987, 2417.
32. (e) Martin, P.; Steiner, E.; Streith, J.; Winker, T.; Bellus, D., Tetrahedron 1985, 41, 4057.
33. (f) Nagashima, H.; Ara, K.; Wakamatsu, H.; Itoh, K. J. Chem. Soc., Chem. Commun. 1985, 518.
34. Very recently, iron-based active catalysts which can be used for 2,2-dichlorocarboxylates were reported by Italian chemists; Forti, L.; Ghelfi, F.; Libertini, E.; Pagnoni, U.M.; Soragni, E, Tetrahedron 1997, 53, 17761.
35. For example, Guindon, Y.; Guélin, B.; Chabot, C.; Ogilvie, W. J. Am. Chem. Soc., 1996, 118, 12528, and references cited therein.
36. Recently, the copper-amine systems are widely used as a catalyst for living radical polymerization, see: (a) Wang, J. S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614.
37. (b) Patten, T. E.; Xia, J.; Abernathy, T.; Matyjaszewski, K. Science 1996, 272, 866.
38. (c) Matyjaszewski, K.; Patten, T. E.; Xia, J. J. Am. Chem. Soc. 1997, 119, 674. and references therein.
39. Keller, R. N.; Wycoff, H. D., Inorg. Synth. 1946, 2, 1.