Palladium-mediated ring opening of hydroxycyclopropanes

Organic Letters

Volumn 2, Issue 2, 2000, Pages 147-149

  Park, Soon Bong ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000692217     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991250r     Document Type: Article

References (35)

1. For general reviews, see: (a) Gibson, D. H.; DePuy, C. H. Chem. Rev. 1974, 74, 605.
2. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
3. (c) Battiste, M. A.; Coxon, J. M. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, U.K., 1987; Chapter 6.
4. (d) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
5. (e) Trost, B. M. Top. Curr. Chem. 1986, 133,
6. For recent representative examples, see: (a) Gassman, P. G.; Bonser, S. M. Tetrahedron Lett. 1983, 24, 3431.
7. (b) Campbell, W. H.; Jennings, P. W. Organometallics 1983, 2, 1460.
8. (c) Blomberg, M. R. A.; Siegbahn, P. E. M.; Bäckvall, J. E. J. Am. Chem. Soc. 1987, 109, 4450.
9. (d) Jennings, P. W.; Johnson, L. L. Chem. Rev. 1994, 94, 2241.
10. (e) Kocovsky, P.; Srogl, J.; Pour, M.; Gogoll, A. J. Am. Chem. Soc. 1994, 116, 186 and references therein.
11. (f) Hayashi, M.; Ohmatsu, T.; Meng, Y.-P.; Saigo, K. Angew. Chem., Int. Ed. 1998, 37, 837.
12. (g) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940.
13. (a) Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1.
14. (b) Ikura, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 1520.
15. (c) Ryu, I.; Ikura, K.; Tamura, Y.; Maenaka, J.; Ogawa, A.; Sonoda, N. Synlett 1994, 941.
16. (d) Sugimura, T.; Futagawa, T.; Mori, A.; Ryu, I.; Sonoda, N.; Tai, A. J. Org. Chem. 1996, 61, 6100.
17. (e) Hoberg, J. O.; Jennings, P. W. Organometallics 1996, 15, 3902.
18. (f) Beyer, J.; Madsen, R. J. Am. Chem. Soc. 1998, 120, 12137.
19. (g) Ito, Y.; Fujii, S.; Nakatsuka, M.; Kawamoto, F.; Saegusa, T. In Organic Synthesis; Norland, W. E., Ed.; Wiley: New York, 1988; Collect. Vol. 6, p 327.
20. (h) Booker-Milburn, K. I.; Thompson, D. F. J. Chem. Soc., Perkin Trans. 1 1995, 2315.
21. (i) Hoberg, J. O. J. Org. Chem. 1997, 62, 6615.
22. (j) Reference 1e.
23. (k) Cohen, T.; Brockunier, L. Tetrahedron 1989, 45, 2917 and references therein.
24. (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244.
25. (b) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294.
26. (c) Kulinkovich, O. G.; Sorokin, V. L.; Kel'in, A. V. Zh. Org. Khim. 1993, 29, 66.
27. (a) Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291.
28. (b) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
29. (c) Lee, J.; Ha, J. D.; Cha, J. K. J. Am. Chem. Soc. 1997, 119, 8127.
30. (d) Ha, J. D.; Lee, J.; Blackstock, S. C.; Cha, J. K. J. Org. Chem. 1998, 63, 8510.
31. Cf.: Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645.
32. For a unique role of DMSO, see: (a) Kagan, H. B.; Ronan, B. Rev. Heteroat. Chem. 1992, 1, 92.
33. (b) Larock, R. C.; Hightower, T. R. J. Org. Chem 1993, 58, 5298.
34. (c) Semmelhack, M. F.; Kim, C. R.; Dobler, W.; Meier, M. Tetrahedron Lett. 1989, 30, 4925.
35. 3 at -20 °C (20 min) resulted in a Nazarov reaction to afford the fused cyclopentenone product in 61% yield.