The first example of an amide-carbonyl stabilized oxiranyl anion: Generation from epoxysilane, its properties, and trapping with electrophiles

Heterocycles

Volumn 59, Issue 1, 2003, Pages 137-147

  Satoh, Tsuyoshi ^a   Shimura, Takayuki ^a   Sakai, Ken ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALDEHYDE; AMIDE; AMMONIUM DERIVATIVE; CARBONYL DERIVATIVE; EPOXIDE; ETHYLENE OXIDE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET IRRADIATION;

EID: 0037224395     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-02-S6     Document Type: Article

References (45)

1. (a) H. O. House and R. S. Ro, J. Am. Chem. Soc., 1958, 80, 2428.
2. (b) A. C. Cope, P. A. Trumbull, and E. R. Trumbull, J. Am. Chem. Soc., 1958, 80, 2844.
3. (c) J. K. Crandall and L.-H. C. Lin, J. Am. Chem. Soc., 1967, 8 9, 4526.
4. (d) J. K. Crandall and L.-H. C. Lin, J. Am. Chem. Soc., 1967, 89, 4527.
5. (e) T. H. Chan, P. W. K. Lau, and M. P. Li, Tetrahedron Lett., 1976, 2667.
6. (f) T. H. Chan and B. S. Ong, J. Org. Chem., 1978, 43, 2994.
7. (g) I. Hasan and Y. Kishi, Tetrahedron Lett., 1980, 21, 4229.
8. (h) H. Tomioka, T. Suzuki, K. Oshima, and H. Nozaki, Tetrahedron Lett., 1982, 23, 3387.
9. (i) J. K. Crandall and M. Apparu, Org. React., 1983, 29, 345.
10. (j) T. Satoh, Y. Kaneko, and K. Yamakawa, Tetrahedron Lett., 1986, 27, 2379.
11. (k) T. Satoh, Y. Kaneko, and K. Yamakawa, Bull. Chem. Soc. Jpn., 1986, 59, 2463.
12. Recent publications: (l) L. Dechoux, E. Doris, and C. Mioskowski, Chem. Commun., 1996, 549.
13. (m) D. M. Hodgson and R. E. Morriott, Tetrahedron Lett., 1997, 38, 519.
14. (n) D. M. Hodgson and R. E. Marriott, Tetrahedron Lett., 1997, 38, 887.
15. (o) C. Agami, L. Dechoux, E. Doris, and C. Mioskowski, Tetrahedron Lett., 1997, 38, 4071.
16. (p) D. M. Hodgson and G. P. Lee, Tetrahedron: Asymmetry, 1997, 8, 2303.
17. (q) D. M. Hodgson, G. P. Lee, R. E. Marriott, A. J. Thompson, R. Wisedale, and J. Witherington, J. Chem. Soc., Perkin Trans. 1, 1998, 2151.
18. (r) D. M. Hodgson, C. R. Maxwell, and I. R. Matthews, Synlett, 1998, 1349.
19. (s) D. M. Hodgson and L. A. Robinson, Chem. Commun., 1999, 309.
20. (t) D. M. Hodgson, C. R. Maxwell, and I. R. Matthews, Tetrahedron: Asymmetry, 1999, 10, 1847.
21. (u) D. M. Hodgson, L. A. Robinson, and M. L. Jones, Tetrahedron Lett., 1999, 40, 8637.
22. (v) L. Dechoux, C. Agami, E. Doris, and C. Mioskowski, J. Org. Chem., 1999, 64, 9279.
23. (w) O. Arjona, R. Menchaca, and J. Plumet, Tetrahedron, 2000, 56, 3901.
24. (x) V. Capriati, S. Florio, R. Luisi, V. Russo, and A. Salomone, Tetrahedron Lett., 2000, 41, 8835.
25. Recent reviews for the chemistry of the oxiranyl anions: (a) T. Satoh, Chem. Rev., 1996, 96, 3303. (b) E. Doris, L. Dechoux, and C. Mioskowski, Synlett, 1998, 337.
26. Recent reviews for the chemistry of the oxiranyl anions: (a) T. Satoh, Chem. Rev., 1996, 96, 3303. (b) E. Doris, L. Dechoux, and C. Mioskowski, Synlett, 1998, 337.
27. (a) Y. Mori, J. Syn. Org. Chem. Jpn., 1997, 55, 176.
28. (b) Y. Mori, K. Yaegashi, and H. Furukawa, J. Org. Chem., 1998, 63, 6200.
29. (c) Y. Mori, K. Yaegashi, and H. Furukawa, Tetrahedron Lett., 1999, 40, 7239.
30. (d) Y. Mori, H. Furuta, T. Takase, S. Mitsuoka, and H. Furukawa, Tetrahedron Lett., 1999, 40, 8019.
31. (e) K. Kuramochi, H. Itaya, S. Nagata, K. Takao, and S. Kobayashi, Tetrahedron Lett., 1999, 40, 7367.
32. (f) K. Kuramochi, S. Nagata, H. Itaya, K. Takao, and S. Kobayashi, Tetrahedron Lett., 1999, 40, 7371.
33. (a) T. Satoh and K. Horiguchi, Tetrahedron Lett., 1995, 36, 8235.
34. (b) T. Satoh, S. Kobayashi, S. Nakanishi, K. Horiguchi, and S. Irisa, Tetrahedron, 1999, 55, 2515.
35. (a) J. J. Eisch and J. E. Galle, J. Organomet. Chem., 1976, 121, C10.
36. (b) J. J. Eisch and J. E. Galle, J. Org. Chem., 1990, 55, 4835.
37. M. Shipman, H. R. Thorpe, and I. R. Clemens, Tetrahedron, 1998, 54, 14265.
38. M. Zhao, J. Li, Z. Song, R. Desmond, D. M. Tschaen, E. J. J. Grabowski, and P. J. Reider, Tetrahedron Lett., 1998, 39, 5323.
39. M. Bodanszky and A. Bodanszky, "The Practice of Peptide Synthesis" pp. 122-123, Springer-Verlag, Berlin, 1984.
40. N. Ono, T. Yamada, T. Saito, K. Tanaka, and A. Kaji, Bull. Chem. Soc. Jpn., 1978, 51, 2401.
41. G. M. Sheldrick, Empirical Absorption Correction Program SADABS, Universitat Gottingen, 1996.
42. G. M. Sheldrick, SHELXS-97: Program for Crystal Structure Solution. University of Gottingen, Germany, 1997.
43. G. M. Sheldrick, SHELXL-97: Program for Crystal Structure Refinement. University of Gottingen, Germany, 1997.
44. K. Sakai, KenX: Program Assisting Shelxl Structure Refinements. Science University of Tokyo, Japan, 2001.
45. teXsan: Single Crystal Structure Analysis Software, Version 1. 10. Molecular Structure Corp., The Woodlands, TX 77381, 1999.