One- And Two-Electron Reactions from the Rearrangement of α-Ketocyclopropanes by O-Stannyl Ketyls

Journal of Organic Chemistry

Volumn 62, Issue 26, 1997, Pages 9159-9164

  Enholm, Eric J ^a   Jia, Zhaozhong J ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001286848     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971287u     Document Type: Article

References (64)

1. (a) Pereyre, M.; Godet, J. Y. Tetrahedron Lett. 1970, 11, 3653.
2. (b) Mariano, P. S.; Bay, E. J. Org. Chem. 1980, 45, 1763.
3. (c) Davies, A. G.; Godet, J.-Y.; Muggleton, B.; Pereyre, M. J. Chem. Soc., Chem. Commun. 1976, 813, 814;
4. (d) Castaing, M.; Pereyre, M.; Ratier, M.; Blum, P. M.; Davies, A. G. J. Chem. Soc., Perkin Trans. II 1979, 589.
5. (e) Godet, J.-Y.; Pereyre, M. Acad. Sci. Paris 1971, 1183.
6. (f) Godet, J.-Y.; Pereyre, M. J. Orgmet. Chem. 1972, 40, C23.
7. (g) Godet, J.-Y.; Davies, A. G.; Muggleton, B.; Pereyre, M. J. Chem. Soc., Perkin Trans. II 1976, 1719.
8. Pereyre, M.; Quintard, J. P.; Rahm A. Tin in Organic Synthesis; Butterworths: Boston, 1987.
9. For a review, see: Shibata, I.; Baba, A. Org. Prep. Proc. Int. 1994, 26, 87.
10. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986.
11. (b) Ramaiah, M. Tetrahedron 1987, 43, 3541.
12. (c) Curran, D. P. Synthesis 1988, 417, 489.
13. (d) Hart, D. J. Science 1984, 223, 883.
14. (e) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press: New York, 1992.
15. For reviews of ketyl radical anions, see: (a) Hirota, N. In Radical Ions; Kaiser, E. T., Kevan, L., Eds.; Wiley-Interscience: New York, 1968; pp 35-85. (b) Russell, G. A. In Radical Ions Kaiser, E. T., Kevan, L., Eds.; Wiley-Interscience: New York, 1968; pp 87-150. (c) Forrester, A. R.; Hay, J. M.; Thompson, R. H. Organic Chemistry of Stable Free Radicals; Academic Press: New York, 1968; pp 82-90.
16. For reviews of ketyl radical anions, see: (a) Hirota, N. In Radical Ions; Kaiser, E. T., Kevan, L., Eds.; Wiley-Interscience: New York, 1968; pp 35-85. (b) Russell, G. A. In Radical Ions Kaiser, E. T., Kevan, L., Eds.; Wiley-Interscience: New York, 1968; pp 87-150. (c) Forrester, A. R.; Hay, J. M.; Thompson, R. H. Organic Chemistry of Stable Free Radicals; Academic Press: New York, 1968; pp 82-90.
17. For reviews of ketyl radical anions, see: (a) Hirota, N. In Radical Ions; Kaiser, E. T., Kevan, L., Eds.; Wiley-Interscience: New York, 1968; pp 35-85. (b) Russell, G. A. In Radical Ions Kaiser, E. T., Kevan, L., Eds.; Wiley-Interscience: New York, 1968; pp 87-150. (c) Forrester, A. R.; Hay, J. M.; Thompson, R. H. Organic Chemistry of Stable Free Radicals; Academic Press: New York, 1968; pp 82-90.
18. (a) Enholm, E. J.; Kinter, K. S. J. Am. Chem. Soc. 1991, 113, 7784.
19. (b) Enholm, E. J.; Xie, Y.; Abboud, K. A. J. Org. Chem. 1995, 60, 1112.
20. (c) Enholm, E. J.; Kinter, K. S. J. Org. Chem. 1995, 60, 4850.
21. (d) Enholm, E. J.; Whitley, P. E. Tetrahedron Lett. 1996, 37, 559.
22. (e) Enholm, E. J.; Jia, Z. J. Tetrahedron Lett. 1996, 37, 1177.
23. (f) Enholm, E. J.; Jia, Z. J. Tetrahedron Lett. 1995, 36, 6819.
24. (g) Enholm, E. J.; Whitley, P. E. Tetrahedron Lett. 1995, 36, 9157.
25. (h) Enholm, E. J.; Jia, Z. J. J. Chem. Soc., Chem. Commun. 1996, 1567.
26. (i) Enholm, E. J.; Jia, Z. J. J. Org. Chem. 1997, 62, 174.
27. (j) Enholm, E. J.; Whitley, P. E.; Xie, Y.-P. J. Org. Chem. 1996, 61, 5384.
28. For related work, see: (a) Kim, Y. H.; Lee, I. S. Heteroatom Chem. 1992, 3, 509. (b) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6211. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1991, 56, 4112. (d) Kirschberg, T.; Mattay, J. J. Org. Chem. 1996, 61, 8885. (e) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217.
29. For related work, see: (a) Kim, Y. H.; Lee, I. S. Heteroatom Chem. 1992, 3, 509. (b) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6211. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1991, 56, 4112. (d) Kirschberg, T.; Mattay, J. J. Org. Chem. 1996, 61, 8885. (e) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217.
30. For related work, see: (a) Kim, Y. H.; Lee, I. S. Heteroatom Chem. 1992, 3, 509. (b) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6211. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1991, 56, 4112. (d) Kirschberg, T.; Mattay, J. J. Org. Chem. 1996, 61, 8885. (e) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217.
31. For related work, see: (a) Kim, Y. H.; Lee, I. S. Heteroatom Chem. 1992, 3, 509. (b) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6211. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1991, 56, 4112. (d) Kirschberg, T.; Mattay, J. J. Org. Chem. 1996, 61, 8885. (e) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217.
32. For related work, see: (a) Kim, Y. H.; Lee, I. S. Heteroatom Chem. 1992, 3, 509. (b) Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6211. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1991, 56, 4112. (d) Kirschberg, T.; Mattay, J. J. Org. Chem. 1996, 61, 8885. (e) Kirschberg, T.; Mattay, J. Tetrahedron Lett. 1994, 35, 7217.
33. (a) Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
34. (b) For a discussion of tin enolate geometry in the aldol reaction, see: Heathcock, C. H. In The Aldol Addition Reaction in Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 136-144.
35. (a) House, H. O.; Crumrine, D. S.; Teranishi, A. Y.; Olmstead, H. D. J. Am. Chem. Soc. 1973, 95, 3310.
36. (b) Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106.
37. Heathcock, C. H.; Pirrung, M. C.; Sohn, J. E. J. Org. Chem. 1979, 44, 4294.
38. (a) Kosugi, M.; Kurino, K.; Takayama, K.; Migita, T. J. Organomet. Chem. 1973, 56, C11.
39. (b) Grignon, J.; Pereyre, M. J. Organomet. Chem. 1973, 61, C33.
40. (c) Grignon, J.; Servens, C.; Pereyre, M. J. Organomet. Chem. 1975, 96, 225.
41. (a) Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829.
42. (b) Keck, G. E.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron, 1985, 41, 4079.
43. (a) Webb, R. R., II; Danishefsky, S. Tetrahedron Lett. 1983, 24, 1357.
44. (b) Migita, T.; Nagai, K.; Kosugi, M. Bull. Chem. Soc. Jpn. 1983, 56, 2480.
45. (c) Ono, N.; Zinsmeister, K.; Kaji, A. Bull. Chem. Soc. Jpn. 1985, 58, 1069.
46. (d) Russell, G. A.; Herold, L. L. J. Org. Chem. 1985, 50, 1037.
47. (e) Keck, G. E.; Kachensky, D. F.; Enholm, E. J. J. Org. Chem. 1985, 50, 4317.
48. (f) Hanessian, S.; Alpegiani, M. Tetrahedron Lett. 1986, 27, 4857.
49. (g) Groninger, K. S.; Jager, K. F.; Giese, B. Liebigs Ann. Chem. 1987, 731.
50. (h) Kano, S.; Yokomatsu, T.; Shibuya, S. J. Org. Chem. 1989, 54, 513.
51. (i) Chu, C. K.; Doboszewski, B.; Schmidt, W.; Ullas, G. V.; Roey, P. V. J. Org. Chem. 1989, 54, 2767.
52. (j) Kelly, M. J.; Newton, R. F.; Roberts, S. M.; Whitehead, J. F. J. Chem. Soc., Perkin Trans. 1 1990, 2352.
53. (k) Blaszczak, L. C.; Armour, H. K.; Halligan, N. G. Tetrahedron Lett. 1990, 31, 5693.
54. (l) Ferrier, R. J.; Lee, C.-K; Wood, T. A. J. Chem. Soc., Chem. Commun. 1991, 690.
55. (m) Hamon, D. P. G. Massy-Westropp, R. A.; Razzino, P. J. Chem. Soc., Chem. Commun. 1991, 722.
56. (n) Paulsen, H.; Matschulat, P. Liebigs Ann. Chem. 1991, 487.
57. (o) Takuwa, A.; Nishigaichi, Y.; Iwamoto, H. Chem. Lett. 1991, 1013.
58. (p) Hasegawa, E.; Ishiyama, K.; Horaguchi, T.; Shimizu, T. Tetrahedron Lett. 1991, 32, 2029.
59. (q) Yoshida, M.; Morinaga, Y.; Ueda, M.; Kamigata, N.; Iyoda, M. Chem. Lett. 1992, 227.
60. (r) Waglund, T.; Claesson, A. Acta Chem. Scand. 1992, 46, 73.
61. (s) Itoh, Y.; Haraguchi, K.; Tanaka, H.; Matsumoto, K.; Nakamura, K. T.; Miyasaka, T. Tetrahedron Lett. 1995, 36, 3867.
62. (t) Roe, R. A.; Boojamra, C. G.; Griggs, J. L.; Bertozzi, C. R. J. Org. Chem. 1996, 61, 6442.
63. Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140.
64. Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.