Formation of 3-pyrrolin-2-ones via 5-endo-trig cyclization

Heterocycles

Volumn 63, Issue 5, 2004, Pages 1009-1012

  Naitoh, Ruri ^a   Nakamura, Yayoi ^a   Katano, Emi ^a   Nakamura, Yohoko ^a   Okada, Emi ^a   Asaoka, Morio ^a  

^a JAPAN WOMEN'S UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 PYRROLIN 2 ONE DERIVATIVE; ANION; BENZYL DERIVATIVE; DEUTERIUM; HETEROCYCLIC COMPOUND; N BENZYL 3 PHENYLSULFANYL 2 PROPENAMIDE DERIVATIVE; PHENYL GROUP; PROPYLENE; PYRROLINE DERIVATIVE; SULFATE; UNCLASSIFIED DRUG;

5 ENDO TRIG CYCLIZATION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 2442454610     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-04-10018     Document Type: Article

References (24)

1. a) T. Shinozuka, Y. Kikori, M. Asaoka, and H. Takei, J. Chem. Soc., Perkin Trans. 1, 1996, 119.
2. b) T. Shinozuka, T. Utsumi, M. Inagaki, and M. Asaoka, J. Chem. Soc., Perkin Trans. 1, 1999, 2433.
3. c) N. Sadayori, A. Kawatoh, R. Sakurazawa, T. Utsumi, M. Inagaki, and M. Asaoka, Heterocycles, 2002, 58, 181.
4. a) J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734.
5. b) J. E. Baldwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman, and R. C. Thomas, J. Chem. Soc., Chem. Commun., 1976, 736.
6. c) J. E. Baldwin, R. C. Thomas, L. Kruse, and L. Silberman, J. Org. Chem., 1977, 42, 3846.
7. For some examples of pyrrolidine formation via anionic 5-endo cyclization, see: a) J. Ichikawa, M. Fujiwara, Y. Wada, T. Okauchi, and T. Minami, Chem. Commun., 2000, 1887.
8. b) J. Ichikawa, Y. Wada, T. Okauchi, and T. Minami, Chem. Commun., 1997, 1537.
9. c) D. Craig, P. S. Jones, and G. J. Rowlands, Synlett., 1997, 1423.
10. d) D. W. Knight, A. L. Redfern, and J. Gilmore, Tetrahedron Lett., 1998, 39, 8909.
11. e) M. B. Berry, D. Craig, P. S. Jones, and G. J. Rowlands, Chem. Commun., 1997, 2141.
12. f) S.-S. P. Chou and T.-M. Yuan, Synthesis, 1991, 171.
13. g) A. D. Jones and D. W. Knight, Chem. Commun., 1996, 915.
14. h) A. Padwa and B. H. Norman, J. Org. Chem., 1990, 55, 4801.
15. For some examples of tetrahydrofuran formation via 5-endo cyclization, see: a) D. Craig, J. N. Ikin, N. Mathews, and A. M. Smith, Tetrahedron Lett., 1995, 36, 7531.
16. b) S. P. Bew, J. M. Barks, D. W. Knight, and R. J. Middleton, Tetrahedron Lett., 2000, 41, 4447.
17. a) J. Clayden, D. W. Watson, M. Helliwell, and M. Chambers, Chem. Commun., 2003, 2582.
18. b) J. Ichikawa, K. Sakoda, and Y. Wada, Chem. Lett., 2002, 31, 282 and references cited therein.
19. Dearomatizing anionic cyclizations via a closely related mechanism are reported: a) R. A. Bragg and J. Clayden, Tetrahedron Lett., 1999, 40, 8323 and 8327.
20. b) J. Clayden, J. C. Menet, and J. D. Mansfield, Org. Lett., 2000, 2, 4229.
21. c) A. Ahmed, J. Clayden, and M. Rowley, Tetrahedron Lett., 1998, 39, 6103.
22. d) J. Clayden and J. M. Rowley, Chem. Commun., 1998, 297.
23. e) J. Clayden and S. A. Yasin, Chem. Commun., 1999, 231.
24. f) J. Clayden, F. E. Knowles, and C. J. Menet, Synlett, 2003, 1701 and references cited therein.