Titanium tetrachloride-induced three-component coupling reaction of α-haloacylsilane, allylsilane, and carbonyl compound

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4483-4486

  Horiuchi, Yoshihiro ^a   Oshima, Koichiro ^a   Utimoto, Kiitiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001487874     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9602332     Document Type: Article

References (59)

1. (a) Page, P. C. B.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195.
2. (b) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647.
3. (c) Cirillio, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553.
4. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
5. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
6. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
7. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
8. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
9. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
10. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
11. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
12. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
13. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
14. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
15. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
16. Preparation: (a) Miller, J. A.; Zweifel, G. Synthesis 1981. 288. (b) Mandai, T.; Yamaguchi, M.; Nakayama, Y.; Otera, J.; Kawada, M. Tetrahedron Lett. 1985, 26, 2675. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198. (d) Brook, A. G.; Duff, J. M.; Jones, P. F.; Davis, N. R. J. Am. Chem. Soc. 1967, 89, 4431. (e) Corey, E. J.; Seebach, D.; Freedman, R. Ibid. 1967, 89, 434. (f) Soderquist, J. A. Org. Synth. 1989, 68, 25. Reaction: (g) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2509. Idem. Ibid. 1985, 26, 2513. (h) Nakajima, T.; Segi, M.; Mituoka, T.; Honda, M.; Naitou, K. Ibid. 1995, 36, 1667. (i) Kuwajima, I.; Kato, M. J. Chem. Soc., Chem. Commun. 1979, 708. (j) Reich, H. J.; Rusek, J. J.; Olson, R. E. J. Am. Chem. Soc. 1979, 101, 2225. (k) Kuwajima, I.; Matsutani, T.; Enda, J. Tetrahedron Lett. 1984, 25, 5307. (l) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493.
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19. (c) Page, P. C. B.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 5421. Idem Tetrahedron 1990, 46, 2573.
20. (c) Page, P. C. B.; Rosenthal, S. Tetrahedron Lett. 1986, 27, 5421. Idem Tetrahedron 1990, 46, 2573.
21. (d) Hewkin, C. T.; Jackson, R. F. W. J. Chem. Soc., Perkin Trans 1 1991, 3103.
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24. (g) Kuwajima, I.; Matsumoto, K.; Sugahara, S. Ibid. 1980, 525.
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26. (b) Morihata, K.; Horiuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Ibid. 1995, 36, 5555.
27. Allylation with allylmetals: (a) Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198. (b) Sato, T.; Matsumoto, K.; Abe, T.; Kuwajima, I. Bull. Chem. Soc. Jpn. 1984, 57, 2167. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (d) Yanagisawa, A.; Habaue, S.; Yamamoto, H. Tetrahedron 1992, 48, 1969.
28. Allylation with allylmetals: (a) Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198. (b) Sato, T.; Matsumoto, K.; Abe, T.; Kuwajima, I. Bull. Chem. Soc. Jpn. 1984, 57, 2167. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (d) Yanagisawa, A.; Habaue, S.; Yamamoto, H. Tetrahedron 1992, 48, 1969.
29. Allylation with allylmetals: (a) Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198. (b) Sato, T.; Matsumoto, K.; Abe, T.; Kuwajima, I. Bull. Chem. Soc. Jpn. 1984, 57, 2167. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (d) Yanagisawa, A.; Habaue, S.; Yamamoto, H. Tetrahedron 1992, 48, 1969.
30. Allylation with allylmetals: (a) Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Org. Chem. 1989, 54, 5198. (b) Sato, T.; Matsumoto, K.; Abe, T.; Kuwajima, I. Bull. Chem. Soc. Jpn. 1984, 57, 2167. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (d) Yanagisawa, A.; Habaue, S.; Yamamoto, H. Tetrahedron 1992, 48, 1969.
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33. (c) Yasui, K.; Fugami, K.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1995, 60, 1365.
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36. (c) Larson, G. L; Hernandez, D.; de Lopez-Cepero, I. M.; Torres, L. E. J. Org. Chem. 1985, 50, 5260.
37. (d) Corey, E. J.; Rücker, C. Tetrahedron Lett. 1984, 25, 4345.
38. (e) Yamamoto, Y.; Ohdori, K.; Nakatani, M.; Akiba, K. Chem. Lett. 1984, 1967.
39. (f) Fürstner, A.; Kollegger, G.; Weidmann, H. J. Organomet. Chem. 1991, 414, 295.
40. 2 and TMSOTf as Lewis acids resulted in a recovery of 1a, and no allylation product was detected in the reaction mixture.
41. 4 was added at 0°C instead of -78°C, and the resulting mixture was stirred for 30 min at 25°C. The reaction at -78°C gave 3 (53%) along with the recovered starting acylsilane 1c (39%).
42. (a) Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 1295.
43. (b) Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumada, M. Ibid. 1983, 24, 2865.
44. The reaction of 1-propynyltrimethylsilane with 1c provided 5-(tert-butyldimethylsilyl)-2-undecyn-4-one (3g) in 33% yield.
45. 4 in the presence of allyltrimethylsilane resulted in complete recovery of starting material 1c.
46. (a) Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868.
47. (b) Panek, J. S.; Beresis, R. J. Org. Chem. 1993, 58, 809.
48. (c) Panek, J. S.; Jain, N. F. Ibid. 1993, 58, 2345.
49. (d) Danheiser, R. L.; Dixon, B. R.; Glenson, R. W. Ibid. 1992, 57, 6094.
50. (e) Yamazaki, S.; Katoh, S.; Yamabe, S. Ibid. 1992, 57, 4.
51. 2) yield.
52. 2 which suggested that the silane remained attached to the carbon skeleton throughout the reaction.
53. 1,2-Silyl migration: (a) Bideau, F. L.; Gilloir, F.; Nilsson, Y.; Anbert, C.; Malacria, M. Tetrahedron Lett. 1996, 36, 1641. (b) Knölker, H-J.; Graf, R.; Synlett 1994, 131. (c) Monti, H.; Audran, G.; Monti, J.-P.; Leandri, G. Synlett 1994, 403. (d) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (e) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116.
54. 1,2-Silyl migration: (a) Bideau, F. L.; Gilloir, F.; Nilsson, Y.; Anbert, C.; Malacria, M. Tetrahedron Lett. 1996, 36, 1641. (b) Knölker, H-J.; Graf, R.; Synlett 1994, 131. (c) Monti, H.; Audran, G.; Monti, J.-P.; Leandri, G. Synlett 1994, 403. (d) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (e) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116.
55. 1,2-Silyl migration: (a) Bideau, F. L.; Gilloir, F.; Nilsson, Y.; Anbert, C.; Malacria, M. Tetrahedron Lett. 1996, 36, 1641. (b) Knölker, H-J.; Graf, R.; Synlett 1994, 131. (c) Monti, H.; Audran, G.; Monti, J.-P.; Leandri, G. Synlett 1994, 403. (d) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (e) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116.
56. 1,2-Silyl migration: (a) Bideau, F. L.; Gilloir, F.; Nilsson, Y.; Anbert, C.; Malacria, M. Tetrahedron Lett. 1996, 36, 1641. (b) Knölker, H-J.; Graf, R.; Synlett 1994, 131. (c) Monti, H.; Audran, G.; Monti, J.-P.; Leandri, G. Synlett 1994, 403. (d) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (e) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116.
57. 1,2-Silyl migration: (a) Bideau, F. L.; Gilloir, F.; Nilsson, Y.; Anbert, C.; Malacria, M. Tetrahedron Lett. 1996, 36, 1641. (b) Knölker, H-J.; Graf, R.; Synlett 1994, 131. (c) Monti, H.; Audran, G.; Monti, J.-P.; Leandri, G. Synlett 1994, 403. (d) Knölker, H.-J.; Foitzik, N.; Goesmann, H.; Graf, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081. (e) Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1990, 55, 6116.
58. β-Ketosilanes have been known to undergo a facile thermal rearrangement to silyl enol ethers. Brook, A. G. Acc. Chem. Res. 1974, 7, 77. See also ref 7e and 7f.
59. Aldol reaction of β-ketosilane with aldehyde in the presence of a Lewis acid have been reported. Kuwajima, I.; Inoue, T.; Sato, T. Tetrahedron Lett. 1978, 4887.