Triethylborane-mediated atom-transfer cyclisation of 2-iodo-N-(prop-2-enyl)acetamides and related compounds

Abstract

The 2-iodo-N-(prop-2-enyl)acetamides 1, upon treatment with triethylborane (0.2–0.6 mol equiv.) in boiling benzene, undergo iodine atom-transfer cyclisation to give the 4-(iodomethyl)pyrrolidin-2-ones 2 in high yields. The method has been applied to the synthesis of γ-lactones.

References

1. (a) T. Sato, Y. Wada, M. Nishimoto, H. Ishibashi and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1989, 879; (b) T. Sato, S. Ishida, H. Ishibashi and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1991, 353; (c) H. Ishibashi, T. S. So, K. Okochi, T. Sato, N. Nakamura, H. Nakatani and M. Ikeda, J. Org. Chem., 1991, 56, 95; (d) T. Sato, K. Tsujimoto, K. Matsubayashi, H. Ishibashi and M. Ikeda, Chem. Pharm. Bull., 1992, 40, 2308; (e) T. Sato, N. Nakamura, K. Ikeda, M. Okada, H. Ishibashi and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1992, 2399; (f) T. Sato, N. Chono, H. Ishibashi and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1995, 1115; (g) H. Ishibashi, C. Kameoka, H. Iriyama, K. Kodama, Y. Sato and M. Ikeda, J. Org. Chem., 1995, 60, 1276; (h) H. Ishibashi, C. Kameoka, K. Kodama and M. Ikeda, Tetrahedron, 1996, 52, 489; (i) H. Ishibashi, K. Kodama, C. Kameoka, H. Kawanami and M. Ikeda, Tetrahedron, 1996, 52, 13 867; (j) H. Ishibashi, C. Kameoka, K. Kodama, H. Kawanami, M. Hamada and M. Ikeda, Tetrahedron, 1997, 53, 9611.
2. (a) R. S. Jolly and T. Livinghouse, J. Am. Chem. Soc., 1988, 110, 7536; (b) D. P. Curran and J. Tamine, J. Org. Chem., 1991, 56, 2746; (c) L. Belvisi, C. Gennari, G. Poli, C. Scolastico, B. Salom and M. Vassallo, Tetrahedron, 1992, 48, 3945.
3. (a) H. Nagashima, H. Wakamatsu, N. Ozaki, T. Ishii, M. Watanabe, T. Tajima and K. Itoh, J. Org. Chem., 1992, 57, 1682; (b) H. Nagashima, N. Ozaki, M. Ishii, K. Seki, M. Washiyama and K. Itoh, J. Org. Chem., 1993, 58, 464 and references cited therein.
4. H. Ishibashi, N. Uemura, H. Nakatani, M. Okazaki, T. Sato, N. Nakamura and M. Ikeda, J. Org. Chem., 1993, 58, 2360.
5. (a) J. A. Seijas, M. P. Vázquez-Tato, L. Castedo, R. J. Estévez, M. G. Ónega and M. Ruíz, Tetrahedron, 1992, 48, 1637; (b) M. Benedetti, L. Forti, F. Ghelfi, U. M. Pagnoni and R. Ronzoni, Tetrahedron, 1997, 53, 14 031.
6. M. Mori, N. Kanda, I. Oda and Y. Ban, Tetrahedron, 1985, 41, 5465.
7. J. Boivin, M. Yousfi and S. Z. Zard, Tetrahedron Lett., 1994, 35, 5629.
8. (a) S. Ozaki, H. Matsushita and H. Ohmori, J. Chem. Soc., Perkin Trans. 1, 1993, 2339; (b) S. Ozaki, H. Matsushita, M. Emoto and H. Ohmori, Chem. Pharm. Bull., 1995, 43, 863.
9. H. C. Brown and M. M. Midland, Angew. Chem., Int. Ed. Engl., 1972, 11, 692.
10. (a) Y. Ichinose, S. Matsunaga, K. Fugami, K. Oshima and K. Utimoto, Tetrahedron Lett., 1989, 30, 3155; (b) Y. Takeyama, Y. Ichinose, K. Oshima and K. Utimoto, Tetrahedron Lett., 1989, 30, 3159; (c) K. Miura, Y. Takeyama, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1991, 64, 1542; (d) K. Matsumoto, K. Miura, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1995, 68, 625; (e) T. J. Woltering and H. M. R. Hoffmann, Tetrahedron, 1995, 51, 7389.
11. A part of this work appeared as a preliminary communication: H. Ishibashi, H. Teranishi, N. Iwamura and M. Ikeda, Heterocycles, 1997, 45, 863.
12. G. Stork and R. Mah, Heterocycles, 1989, 28, 723.
13. F. Rolla, J. Org. Chem., 1981, 46, 3909.
14. B. Cardillo, R. Galeazzi, G. Mobbili, M. Orena and M. Rossetti, Heterocycles, 1994, 38, 2663.