Ethenylation of silyl enol ether with silylethyne

Journal of the American Chemical Society

Volumn 121, Issue 16, 1999, Pages 4074-4075

  Yamaguchi, Masahiko ^a   Tsukagoshi, Toru ^a   Arisawa, Mieko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE; ETHER DERIVATIVE; SILANE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; ISOMER; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033611980     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984022l     Document Type: Article

References (22)

1. For examples, see: Bunnett, J. F.; Creary, X.; Sundberg, J. E. J. Org. Chem. 1976, 41, 1707. Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1983, 839. Moloney, M. G.; Pinhey, J. T. J. Chem. Soc., Chem. Commun. 1984, 965. Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 51.
2. For examples, see: Bunnett, J. F.; Creary, X.; Sundberg, J. E. J. Org. Chem. 1976, 41, 1707. Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1983, 839. Moloney, M. G.; Pinhey, J. T. J. Chem. Soc., Chem. Commun. 1984, 965. Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 51.
3. For examples, see: Bunnett, J. F.; Creary, X.; Sundberg, J. E. J. Org. Chem. 1976, 41, 1707. Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1983, 839. Moloney, M. G.; Pinhey, J. T. J. Chem. Soc., Chem. Commun. 1984, 965. Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 51.
4. For examples, see: Bunnett, J. F.; Creary, X.; Sundberg, J. E. J. Org. Chem. 1976, 41, 1707. Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1983, 839. Moloney, M. G.; Pinhey, J. T. J. Chem. Soc., Chem. Commun. 1984, 965. Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 51.
5. For examples, see: Bunnett, J. F.; Creary, X.; Sundberg, J. E. J. Org. Chem. 1976, 41, 1707. Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1983, 839. Moloney, M. G.; Pinhey, J. T. J. Chem. Soc., Chem. Commun. 1984, 965. Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 51.
6. Seefelder, M. Liebigs Ann. Chem. 1962, 652, 107. Makosza, M. Tetrahedron Lett. 1966, 5489. Formation of 2-ethenylcyclohexanone by the reaction of cyclohexanone and pressurized ethyne in a very low yield was reported. Shuikin, N. I.; Lebedev, B. L.; Nikol'skii, V. G. Izv. Akad. Nauk SSSR, Ser. Khim. 1965, 369; Chem. Abstr. 1965, 62, 14519f.
7. Seefelder, M. Liebigs Ann. Chem. 1962, 652, 107. Makosza, M. Tetrahedron Lett. 1966, 5489. Formation of 2-ethenylcyclohexanone by the reaction of cyclohexanone and pressurized ethyne in a very low yield was reported. Shuikin, N. I.; Lebedev, B. L.; Nikol'skii, V. G. Izv. Akad. Nauk SSSR, Ser. Khim. 1965, 369; Chem. Abstr. 1965, 62, 14519f.
8. Seefelder, M. Liebigs Ann. Chem. 1962, 652, 107. Makosza, M. Tetrahedron Lett. 1966, 5489. Formation of 2-ethenylcyclohexanone by the reaction of cyclohexanone and pressurized ethyne in a very low yield was reported. Shuikin, N. I.; Lebedev, B. L.; Nikol'skii, V. G. Izv. Akad. Nauk SSSR, Ser. Khim. 1965, 369; Chem. Abstr. 1965, 62, 14519f.
9. Seefelder, M. Liebigs Ann. Chem. 1962, 652, 107. Makosza, M. Tetrahedron Lett. 1966, 5489. Formation of 2-ethenylcyclohexanone by the reaction of cyclohexanone and pressurized ethyne in a very low yield was reported. Shuikin, N. I.; Lebedev, B. L.; Nikol'skii, V. G. Izv. Akad. Nauk SSSR, Ser. Khim. 1965, 369; Chem. Abstr. 1965, 62, 14519f.
10. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
11. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
12. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
13. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
14. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
15. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
16. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
17. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
18. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
19. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
20. Oishi, T.; Takechi, H.; Ban, Y. Tetrahedron Lett. 1974, 3757. Koppel, G. A.; Kinnick, M. D. J. Chem. Soc., Chem. Commun. 1975, 473. Metcalf, B. W.; Bonilavri, E. J. Chem. Soc., Chem. Commun. 1978, 914. Bruhn, J.; Heimgartner, H.; Schmid, H. Helv. Chim. Acta 1979, 62, 2630. Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5930. Kowalski, C. J.; Dung, J.-S. J. Am. Chem. Soc. 1980, 102, 7951. Steglich, W.; Wegmann, H. Synthesis 1980, 481. Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251. Clive, D. L. J.; Russell, C. G. J. Chem. Soc., Chem. Commun. 1981, 434. Ohnuma, T.; Hata, N.; Fujiwara, H.; Ban, Y. J. Org. Chem. 1982, 47, 4713. Kende, A. S.; Fludzinski, P.; Hill, J. H.; Swenson, W.; Clardy, J. J. Am. Chem. Soc. 1984, 106, 3551.
21. Yamaguchi, M.; Hayashi, A.; Hirama, M. Chem. Lett. 1995, 1093.
22. Yamaguchi, M.; Sotokawa, T.; Hirama, M. J. Chem. Soc., Chem. Commun. 1997, 743.