Catalysis of chlorosilane on the ring-expansion of cyclic acetals bearing a carbene precursor. Lewis acid-base effect on the oxonium ylide intermediate

Chemical Communications

Volumn , Issue 14, 1999, Pages 1339-1340

  Mori, Takashi ^a   Oku, Akira ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; RHODIUM; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; DECOMPOSITION;

EID: 0033591875     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903928g     Document Type: Article

References (24)

1. For carbonyl ylides, see reviews: A. Padwa and S. F. Hornbuckle, Chem. Rev., 1991, 91, 263; T. Ye and M. A. Mckervey, Chem. Rev. 1994, 94, 1091; A. Padwa and M. D. Weingarten, Chem. Rev., 1996, 96, 223.
2. For carbonyl ylides, see reviews: A. Padwa and S. F. Hornbuckle, Chem. Rev., 1991, 91, 263; T. Ye and M. A. Mckervey, Chem. Rev. 1994, 94, 1091; A. Padwa and M. D. Weingarten, Chem. Rev., 1996, 96, 223.
3. For carbonyl ylides, see reviews: A. Padwa and S. F. Hornbuckle, Chem. Rev., 1991, 91, 263; T. Ye and M. A. Mckervey, Chem. Rev. 1994, 94, 1091; A. Padwa and M. D. Weingarten, Chem. Rev., 1996, 96, 223.
4. (a) I. Naito, A. Oku, N. Ohtani, Y. Fujiwara and Y. Tanimoto, J. Chem. Soc., Perkin Trans. 2, 1996, 725;
5. (b) H. Tomioka, N. Kobayashi, S. Murata and T. Ohtawa, J. Am. Chem. Soc., 1991, 113, 8771.
6. F. G. West, B. N. Naidu and R. W. Tester, J. Org. Chem., 1994, 59, 6892; J. B. Brogan, C. B. Bauer, R. D. Rogers and C. K. Zerher, Tetrahedron Lett., 1996, 37, 5053; M. P. Doyle, D. G. Ene, D. C. Forbes and J. S. Tedrow, Tetrahedron Lett., 1997, 38, 4367.
7. F. G. West, B. N. Naidu and R. W. Tester, J. Org. Chem., 1994, 59, 6892; J. B. Brogan, C. B. Bauer, R. D. Rogers and C. K. Zerher, Tetrahedron Lett., 1996, 37, 5053; M. P. Doyle, D. G. Ene, D. C. Forbes and J. S. Tedrow, Tetrahedron Lett., 1997, 38, 4367.
8. F. G. West, B. N. Naidu and R. W. Tester, J. Org. Chem., 1994, 59, 6892; J. B. Brogan, C. B. Bauer, R. D. Rogers and C. K. Zerher, Tetrahedron Lett., 1996, 37, 5053; M. P. Doyle, D. G. Ene, D. C. Forbes and J. S. Tedrow, Tetrahedron Lett., 1997, 38, 4367.
9. J. S. Clark, A. G. Dosetter and W. G. Whittingham, Tetrahedron Lett., 1996, 37, 5605; M. P. Doyle, V. Bagheri and E. Claxton, J. Chem. Soc., Chem. Commun., 1990, 46.
10. J. S. Clark, A. G. Dosetter and W. G. Whittingham, Tetrahedron Lett., 1996, 37, 5605; M. P. Doyle, V. Bagheri and E. Claxton, J. Chem. Soc., Chem. Commun., 1990, 46.
11. E. J. Roskamp and C. R. Johnson, J. Am. Chem. Soc., 1986, 108, 6062.
12. For the ring-expansion of bicyclic oxonium ylides, see: A. Oku, S. Ohki, T. Yoshida and K. Kimura, Chem. Commun., 1996, 1077; A. Oku, N. Murai and J. Baird, J. Org. Chem. 1997, 62, 2123; T. Mori, M. Taniguchi, F. Suzuki, H. Doi and A. Oku, J. Chem. Soc., Perkin Trans. 1, 1998, 3623.
13. For the ring-expansion of bicyclic oxonium ylides, see: A. Oku, S. Ohki, T. Yoshida and K. Kimura, Chem. Commun., 1996, 1077; A. Oku, N. Murai and J. Baird, J. Org. Chem. 1997, 62, 2123; T. Mori, M. Taniguchi, F. Suzuki, H. Doi and A. Oku, J. Chem. Soc., Perkin Trans. 1, 1998, 3623.
14. For the ring-expansion of bicyclic oxonium ylides, see: A. Oku, S. Ohki, T. Yoshida and K. Kimura, Chem. Commun., 1996, 1077; A. Oku, N. Murai and J. Baird, J. Org. Chem. 1997, 62, 2123; T. Mori, M. Taniguchi, F. Suzuki, H. Doi and A. Oku, J. Chem. Soc., Perkin Trans. 1, 1998, 3623.
15. For the ring-expansion of bicyclic oxonium ions, see: T. Kamada, G. Quing, M. Abe and A. Oku, J. Chem. Soc., Perkin Trans. 1, 1996, 413; T. Nakata, S. Nomura and H. Matukura, Tetrahedron Lett., 1996, 37, 213, 217 and 6365.
16. For the ring-expansion of bicyclic oxonium ions, see: T. Kamada, G. Quing, M. Abe and A. Oku, J. Chem. Soc., Perkin Trans. 1, 1996, 413; T. Nakata, S. Nomura and H. Matukura, Tetrahedron Lett., 1996, 37, 213, 217 and 6365.
17. A. B. Smith and R. K. Dieter, Tetrahedron, 1981, 37, 2407.
18. When impure TMSC1 was used, the yield of this by-product increased, probably because contaminant HCl reacted with diazo ketone 1a to give it.
19. 3N, decreased the yield of 3a.
20. The Lewis acid character of the silyl cation is described in different reaction systems: S. Murata, M. Suzuki and R. Noyori, J. Am. Chem. Soc., 1980, 102, 3248; H. Sakurai, K. Sasaki and A. Hosomi, Bull. Chem. Soc. Jpn., 1983, 56, 3195; T. Sato, Y. Wakahara and H. Nozaki, Tetrahedron Lett., 1990, 31, 1581; K. T. Hollis and B. Bosnich, J. Am. Chem. Soc., 1995, 117, 4570.
21. The Lewis acid character of the silyl cation is described in different reaction systems: S. Murata, M. Suzuki and R. Noyori, J. Am. Chem. Soc., 1980, 102, 3248; H. Sakurai, K. Sasaki and A. Hosomi, Bull. Chem. Soc. Jpn., 1983, 56, 3195; T. Sato, Y. Wakahara and H. Nozaki, Tetrahedron Lett., 1990, 31, 1581; K. T. Hollis and B. Bosnich, J. Am. Chem. Soc., 1995, 117, 4570.
22. The Lewis acid character of the silyl cation is described in different reaction systems: S. Murata, M. Suzuki and R. Noyori, J. Am. Chem. Soc., 1980, 102, 3248; H. Sakurai, K. Sasaki and A. Hosomi, Bull. Chem. Soc. Jpn., 1983, 56, 3195; T. Sato, Y. Wakahara and H. Nozaki, Tetrahedron Lett., 1990, 31, 1581; K. T. Hollis and B. Bosnich, J. Am. Chem. Soc., 1995, 117, 4570.
23. The Lewis acid character of the silyl cation is described in different reaction systems: S. Murata, M. Suzuki and R. Noyori, J. Am. Chem. Soc., 1980, 102, 3248; H. Sakurai, K. Sasaki and A. Hosomi, Bull. Chem. Soc. Jpn., 1983, 56, 3195; T. Sato, Y. Wakahara and H. Nozaki, Tetrahedron Lett., 1990, 31, 1581; K. T. Hollis and B. Bosnich, J. Am. Chem. Soc., 1995, 117, 4570.
24. The equilibrium was first reported in ref. 2(a), and then by T. Sueda, T. Nagaoka, S. Goto and M. Ochiai, J. Am. Chem. Soc., 1996, 118, 10141.