Indium-mediated substitution of 4-acetoxy-2-azetidinones: Synthesis of 4-allyl-2-azetidinones

Synlett

Volumn , Issue 4, 1999, Pages 447-449

  Kang, Suk Ku ^b   Baik, Tae Gon ^b   Jiao, Xiang Hua ^b   Lee, Kyong Ju ^b   Lee, Cheol Hae ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

^b Sungkyunkwan University   (South Korea)

Author keywords

Allylation; Azetidinones; Indium compounds

Indexed keywords

AZETIDINONE DERIVATIVE; INDIUM;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PHYSICAL CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0032923982     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2652     Document Type: Article

References (33)

1. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
2. Reviews: (a) Cintas, P. Synlett 1995, 1087.
3. (b) Li, C-J. Tetrahedron 1996, 52, 5643.
4. (c) Chan, T. H.; Isaac, M.B. Pure & Appl. Chem. 1996, 68, 919.
5. (d) Hirashita, T.; Inoue, S.; Yamamura, H.; Kawai, M.; Araki, S. J. Organomet. Chem. 1997, 549, 305 and reference thererin.
6. Beuchet, P.; Lee Marret, N.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959.
7. (b) Loh, T-P.; Ho, D, S-C.; Xu, K-C.; Sim, K-Y. Tetrahedron Lett. 1997, 38, 865.
8. (a) Kobayashi, T.; Ishida, N.; Hiraoka, T. J. Chem. Soc., Chem. Commun. 1980, 736.
9. (b) Oida, S.; Yoshida, A.; Ohki, E. Chem. Pharm. Bull. 1980, 28, 3494.
10. (c) Barrett, A. G. M.; Quayle, P. J. Chem. Soc., Chem. Commun. 1981, 1076.
11. (d) Shibasaki, M.; Nishida, A.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1982, 1324.
12. (e) Hirai, K.; Iwano, Y.; Fujimoto, K. Tetrahedron Lett. 1982, 23, 4025.
13. (f) Fuenes, L. M.; Shinkai, I.; Salzmann, T. N. J. Am. Chem. Soc. 1986, 108, 4675.
14. (g) Deziel, R.; Favreau, D. Tetrahedron Lett. 1986, 27, 5687.
15. (h) Nagao, Y.; Kumagai, T.; Tamai, S.; Abe, T.; Kuramoto, Y.; Taga, T.; Aoyagi, S.; Nagase, Y.; Ochiai, M.; Inoue, Y.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 4673.
16. (i) Kim, C. U.; Luh, B.; Partyka, R. A. Tetrahedron Lett. 1987, 28, 507.
17. (j) Prasad, J. S.; Liebeskind, L. S. ibid. 1988, 29, 4253.
18. (k) Harata, J-i.; Nishi, K.; Kikuchi, K.; Matsuda, S.; Tamaru, Y.; Kita, Y. Chem. Pharm. Bull. 1989, 37, 2338.
19. (l) Mori, M.; Oida, S. Bioorg. & Med. Chem. Lett. 1993, 3, 2389.
20. (m) Itani, H.; Uyeo, S. Synlett. 1995, 213.
21. (n) Kondo, K.; Seki, M.; Kuroda, T.; Tamanaka, T.; Iwasaki, T. J. Org. Chem. 1997, 62, 2884.
22. (a) Hanessian, S.; Desilets, D.; Bennani, Y. L. J. Org. Chem. 1990, 55, 3098.
23. (b) Koller, W.; Linkies, A.; Pietsch, H.; Rehling, H.; Reuschling, D. Tetrahedron Lett. 1982, 23, 1545.
24. (a) Kraus, G. A.; Neuenschwander, K. J. Chem. Soc. Chem. Commun. 1982, 134.
25. (b) Kang, J.; Kim, J.; Lee, K-J. Synlett 1991, 885.
26. (c) Oumoch, S.; Rousseau, G. Bioorg. & Med. Chem. Lett. 1994, 4, 2841.
27. (d) Crombie, L.; Haigh, D.; Jones, R. C. F.; Mat Zin, Ab, R. J. Chem. Soc., Perkin Trans. I 1993, 2055.
28. Fliri, H.; Mak, C-P. J. Org. Chem. 1985, 50, 3438.
29. (b) Fujimoto, K.; Iwano, Y.; Hirai, K. Bull. Chem. Soc. Jpn. 1986, 59, 1363.
30. (c) Haruta, J-I.; Nishi, K.; Kikuchi, K.; Matsuda, S.; Tamaru, Y.; Kita, Y. Chem. Pharm. Bull. 1989, 37, 2338.
31. Uyeo, S.; Itani, H. Tetrahedron. Lett. 1991, 32, 2143.
32. f = 0.73) to afford 3a (83 mg, 88%).
33. 13NO: C, 69.08; H, 9.35; N, 10.07%.