Intramolecular hydroxycyclopropanation of ω-vinyl carboxylic esters

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 291-292

  Lee, Jinhwa ^a   Kang, Chul Hyun ^a   Kim, Heejin ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1642548109     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953055n     Document Type: Article

References (31)

1. For recent reviews in this area, see: (a) Reetz, M. T. In Organometallics in Synthesis: Schlosser, M , Ed.: Wiley: New York, 1994; Chapter 3 (b) Weidmann, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 22, 31. (c) Sato, F J. Organomet. Chem 1985, 285, 53 (d) Dzhemilev, U. M., Vostrikova, O. S.; Tolstikov, G. A. J. Organomet. Chem. 1986, 304, 17. (e) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (f) Negishi, E., Takahashi, T. Acc. Chem Res. 1994, 27, 124.
2. For recent reviews in this area, see: (a) Reetz, M. T. In Organometallics in Synthesis: Schlosser, M , Ed.: Wiley: New York, 1994; Chapter 3 (b) Weidmann, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 22, 31. (c) Sato, F J. Organomet. Chem 1985, 285, 53 (d) Dzhemilev, U. M., Vostrikova, O. S.; Tolstikov, G. A. J. Organomet. Chem. 1986, 304, 17. (e) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (f) Negishi, E., Takahashi, T. Acc. Chem Res. 1994, 27, 124.
3. For recent reviews in this area, see: (a) Reetz, M. T. In Organometallics in Synthesis: Schlosser, M , Ed.: Wiley: New York, 1994; Chapter 3 (b) Weidmann, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 22, 31. (c) Sato, F J. Organomet. Chem 1985, 285, 53 (d) Dzhemilev, U. M., Vostrikova, O. S.; Tolstikov, G. A. J. Organomet. Chem. 1986, 304, 17. (e) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (f) Negishi, E., Takahashi, T. Acc. Chem Res. 1994, 27, 124.
4. For recent reviews in this area, see: (a) Reetz, M. T. In Organometallics in Synthesis: Schlosser, M , Ed.: Wiley: New York, 1994; Chapter 3 (b) Weidmann, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 22, 31. (c) Sato, F J. Organomet. Chem 1985, 285, 53 (d) Dzhemilev, U. M., Vostrikova, O. S.; Tolstikov, G. A. J. Organomet. Chem. 1986, 304, 17. (e) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (f) Negishi, E., Takahashi, T. Acc. Chem Res. 1994, 27, 124.
5. For recent reviews in this area, see: (a) Reetz, M. T. In Organometallics in Synthesis: Schlosser, M , Ed.: Wiley: New York, 1994; Chapter 3 (b) Weidmann, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 22, 31. (c) Sato, F J. Organomet. Chem 1985, 285, 53 (d) Dzhemilev, U. M., Vostrikova, O. S.; Tolstikov, G. A. J. Organomet. Chem. 1986, 304, 17. (e) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (f) Negishi, E., Takahashi, T. Acc. Chem Res. 1994, 27, 124.
6. For recent reviews in this area, see: (a) Reetz, M. T. In Organometallics in Synthesis: Schlosser, M , Ed.: Wiley: New York, 1994; Chapter 3 (b) Weidmann, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1983, 22, 31. (c) Sato, F J. Organomet. Chem 1985, 285, 53 (d) Dzhemilev, U. M., Vostrikova, O. S.; Tolstikov, G. A. J. Organomet. Chem. 1986, 304, 17. (e) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047. (f) Negishi, E., Takahashi, T. Acc. Chem Res. 1994, 27, 124.
7. 2 and stoichiometric i-PrMgBr (a) Sato, F.; Jinbo, T.; Sato, M. Tetrahedron Lett. 1980, 21, 2175. (b) Barr, K. J.; Berk, S. C., Buchwald, S. L. J. Org. Chem. 1994, 59, 4323 and references cited therein.
8. 2 and stoichiometric i-PrMgBr (a) Sato, F.; Jinbo, T.; Sato, M. Tetrahedron Lett. 1980, 21, 2175. (b) Barr, K. J.; Berk, S. C., Buchwald, S. L. J. Org. Chem. 1994, 59, 4323 and references cited therein.
9. See, inter alia: (a) Buchwald, S. L ; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544. (b) RajanBabu, T. V., Nugent, W A ; Taber, D. F.: Fagan, P. J. J. Am. Chem Soc. 1988, 110, 7128. (c) Lund, E. C.: Livinghouse, T. J. Org. Chem. 1989, 54, 4487 (d) Takahashi, T.; Seki, T.: Nitto, Y.; Saburi, M.; Rousset, C. J.: Negishi. E J. Am. Chem. Soc. 1991, 113, 6266. (e) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268 (f) Hoveyda, A H.; Xu, Z.; Morken, J. P ; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950 (g) Negishi, E (guest editor). Tetrahedron 1995, 51, 4255-4281.
10. See, inter alia: (a) Buchwald, S. L ; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544. (b) RajanBabu, T. V., Nugent, W A ; Taber, D. F.: Fagan, P. J. J. Am. Chem Soc. 1988, 110, 7128. (c) Lund, E. C.: Livinghouse, T. J. Org. Chem. 1989, 54, 4487 (d) Takahashi, T.; Seki, T.: Nitto, Y.; Saburi, M.; Rousset, C. J.: Negishi. E J. Am. Chem. Soc. 1991, 113, 6266. (e) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268 (f) Hoveyda, A H.; Xu, Z.; Morken, J. P ; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950 (g) Negishi, E (guest editor). Tetrahedron 1995, 51, 4255-4281.
11. See, inter alia: (a) Buchwald, S. L ; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544. (b) RajanBabu, T. V., Nugent, W A ; Taber, D. F.: Fagan, P. J. J. Am. Chem Soc. 1988, 110, 7128. (c) Lund, E. C.: Livinghouse, T. J. Org. Chem. 1989, 54, 4487 (d) Takahashi, T.; Seki, T.: Nitto, Y.; Saburi, M.; Rousset, C. J.: Negishi. E J. Am. Chem. Soc. 1991, 113, 6266. (e) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268 (f) Hoveyda, A H.; Xu, Z.; Morken, J. P ; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950 (g) Negishi, E (guest editor). Tetrahedron 1995, 51, 4255-4281.
12. See, inter alia: (a) Buchwald, S. L ; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544. (b) RajanBabu, T. V., Nugent, W A ; Taber, D. F.: Fagan, P. J. J. Am. Chem Soc. 1988, 110, 7128. (c) Lund, E. C.: Livinghouse, T. J. Org. Chem. 1989, 54, 4487 (d) Takahashi, T.; Seki, T.: Nitto, Y.; Saburi, M.; Rousset, C. J.: Negishi. E J. Am. Chem. Soc. 1991, 113, 6266. (e) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268 (f) Hoveyda, A H.; Xu, Z.; Morken, J. P ; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950 (g) Negishi, E (guest editor). Tetrahedron 1995, 51, 4255-4281.
13. See, inter alia: (a) Buchwald, S. L ; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544. (b) RajanBabu, T. V., Nugent, W A ; Taber, D. F.: Fagan, P. J. J. Am. Chem Soc. 1988, 110, 7128. (c) Lund, E. C.: Livinghouse, T. J. Org. Chem. 1989, 54, 4487 (d) Takahashi, T.; Seki, T.: Nitto, Y.; Saburi, M.; Rousset, C. J.: Negishi. E J. Am. Chem. Soc. 1991, 113, 6266. (e) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268 (f) Hoveyda, A H.; Xu, Z.; Morken, J. P ; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950 (g) Negishi, E (guest editor). Tetrahedron 1995, 51, 4255-4281.
14. See, inter alia: (a) Buchwald, S. L ; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544. (b) RajanBabu, T. V., Nugent, W A ; Taber, D. F.: Fagan, P. J. J. Am. Chem Soc. 1988, 110, 7128. (c) Lund, E. C.: Livinghouse, T. J. Org. Chem. 1989, 54, 4487 (d) Takahashi, T.; Seki, T.: Nitto, Y.; Saburi, M.; Rousset, C. J.: Negishi. E J. Am. Chem. Soc. 1991, 113, 6266. (e) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268 (f) Hoveyda, A H.; Xu, Z.; Morken, J. P ; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950 (g) Negishi, E (guest editor). Tetrahedron 1995, 51, 4255-4281.
15. See, inter alia: (a) Buchwald, S. L ; Watson, B. T.; Huffman, J. C. J. Am. Chem. Soc. 1987, 109, 2544. (b) RajanBabu, T. V., Nugent, W A ; Taber, D. F.: Fagan, P. J. J. Am. Chem Soc. 1988, 110, 7128. (c) Lund, E. C.: Livinghouse, T. J. Org. Chem. 1989, 54, 4487 (d) Takahashi, T.; Seki, T.: Nitto, Y.; Saburi, M.; Rousset, C. J.: Negishi. E J. Am. Chem. Soc. 1991, 113, 6266. (e) Knight, K. S.; Waymouth, R. M. J. Am. Chem. Soc. 1991, 113, 6268 (f) Hoveyda, A H.; Xu, Z.; Morken, J. P ; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950 (g) Negishi, E (guest editor). Tetrahedron 1995, 51, 4255-4281.
16. (a) Kulinkovich, O. G.; Sviridov, S V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244.
17. (b) Kulinkovich, O. G.; Sviridov, S V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294
18. (c) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234.
19. (d) Kulinkovich, O. G , Vasilevskii, D. A.: Savchenko, A. I., Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428.
20. de Meijere, A.; Kozhushkov, S. I.; Spaeth, T ; Zefirov, N. S. J. Org. Chem. 1993, 58, 502.
21. Corey, E. J.; Rao, S A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345.
22. Lee, J ; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919.
23. 2Zr") and 2 equiv of i-PrMgBr: Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881. See also: Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 1295.
24. 2Zr") and 2 equiv of i-PrMgBr: Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881. See also: Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 1295.
25. Subsequent to submission of our manuscript, Sato and Kasatkin reported a stereoselective synthesis of trans-1.2-disubstituted cyclopropanols from esters of 3-butenols (cf. entries 14 and 15, Table 1) under similar reaction conditions: Kasatkin, A., Sato, F. Tetrahedron Lett. 1995, 36, 6079.
26. Some bicyclo[n. 1.0]-l-alkanols were previously prepared by Simmons-Smith cyclopropanation of trimethylsilyl cycloalkenyl ethers, followed by hydrolysis under mild conditions: (a) Murai, S.; Aya, T.: Sonoda, N. J. Org. Chem. 1973, 38, 4354. (b) Rubottom, G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097.
27. Some bicyclo[n. 1.0]-l-alkanols were previously prepared by Simmons-Smith cyclopropanation of trimethylsilyl cycloalkenyl ethers, followed by hydrolysis under mild conditions: (a) Murai, S.; Aya, T.: Sonoda, N. J. Org. Chem. 1973, 38, 4354. (b) Rubottom, G. M.; Lopez, M. I. J. Org. Chem. 1973, 38, 2097.
28. Application of our hydroxycyclopropanation protocol to γ-lactones having an ω-vinyl-substituted tether failed to provide the corresponding ring-enlarged cyclopropanols.
29. 2 has been shown to afford titanacycles in good yield: (a) Hewlett, D. F.: Whitby, R. J. J. Chem. Soc., Chem. Commun. 1990, 1684. (b) Kablaoui, N. M.: Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. (c) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787.
30. 2 has been shown to afford titanacycles in good yield: (a) Hewlett, D. F.: Whitby, R. J. J. Chem. Soc., Chem. Commun. 1990, 1684. (b) Kablaoui, N. M.: Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. (c) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787.
31. 2 has been shown to afford titanacycles in good yield: (a) Hewlett, D. F.: Whitby, R. J. J. Chem. Soc., Chem. Commun. 1990, 1684. (b) Kablaoui, N. M.: Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785. (c) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787.