Stereoselective Synthesis of 2,3-cis-2-Alkyl-5-oxo-3-silyloxycyclopentanecarboxylates using Dirhodium(II)-catalyzed Intramolecular C-H Insertion Reaction of 2-Diazo-3-oxo-5-silyloxyalkanoates

Synlett

Volumn 1997, Issue 2, 1997, Pages 185-186

  Yakura, Takayuki ^a   Yamada, Seiji ^a   Ueki, Akiharu ^a   Ikeda, Masazumi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041801189     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-749     Document Type: Article

References (36)

1. For reviews, see; Doyle, M. P. Chem. Rev. 1986, 86, 919; Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765; Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385; Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091; Padwa, A.; Austin, D. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1797.
2. For reviews, see; Doyle, M. P. Chem. Rev. 1986, 86, 919; Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765; Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385; Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091; Padwa, A.; Austin, D. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1797.
3. For reviews, see; Doyle, M. P. Chem. Rev. 1986, 86, 919; Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765; Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385; Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091; Padwa, A.; Austin, D. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1797.
4. For reviews, see; Doyle, M. P. Chem. Rev. 1986, 86, 919; Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765; Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385; Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091; Padwa, A.; Austin, D. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1797.
5. For reviews, see; Doyle, M. P. Chem. Rev. 1986, 86, 919; Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765; Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385; Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091; Padwa, A.; Austin, D. J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1797.
6. (a) Pirrung M. C., Werner, J. A. J. Am. Chem. Soc. 1986, 108, 6060.
7. (b) Roskamp, E. J.; Johnson, C. R. J. Am. Chem. Soc. 1986, 108, 6062.
8. (c) Eberlein, T. H.; West, F. G.; Tester, R. W. J. Org. Chem. 1992, 57, 3479.
9. (d) Clark, J. S.; Krowiak, S. A.; Street, L. J. Tetrahedron Lett. 1993, 34, 4385.
10. (e) West, F. G.; Eberlein, T. H.; Tester, R. W.; J. Chem. Soc., Perkin Trans. 1 1993, 2857.
11. (f) West, F. G.; Naidu, B. N.; Tester, R. W. J. Org. Chem. 1994, 59, 6892.
12. (g) Pirrung, M. C.; Morehead, A. T., Jr. J. Am. Chem. Soc. 1994, 116, 8991 and references therein.
13. (h) Adams, J.; Poupart, M.-A.; Grenier, L.; Schaller, C.; Ouimet, N.; Frenette, R. Tetrahedron Lett. 1989, 30, 1749.
14. 16
15. The other oxygen substituents such as 2-(ethoxy)ethyloxy and pivaloyloxy groups were ineffective.
16. Both 2a and 3a were found to exist as a >95:5 equilibrium mixture of the keto and enol forms.
17. (a) Taber, D. F.; Ruckle, R. E., Jr. J. Am. Chem. Soc. 1986, 108, 7686.
18. (b) Hashimoto, S.; Watanabe, N.; Ikegami, S. Tetrahedron Lett. 1990, 31, 5173.
19. Taber, D. F.; Amedio, J. C., Jr.; Gulino, F. J. Org. Chem. 1989, 54, 3474.
20. Takahashi, K.; Shiro, M.; Kishi, M. J. Org. Chem. 1988, 53, 3098; Smith, A. B., III; Dunlap, N. K.; Sulikowski, G. A. Tetrahedron Lett. 1988, 29, 439; Maruoka, K.; Shimada, J.; Imoto, H.; Yamamoto, H. Synlett 1994, 519 and references therein.
21. Takahashi, K.; Shiro, M.; Kishi, M. J. Org. Chem. 1988, 53, 3098; Smith, A. B., III; Dunlap, N. K.; Sulikowski, G. A. Tetrahedron Lett. 1988, 29, 439; Maruoka, K.; Shimada, J.; Imoto, H.; Yamamoto, H. Synlett 1994, 519 and references therein.
22. Takahashi, K.; Shiro, M.; Kishi, M. J. Org. Chem. 1988, 53, 3098; Smith, A. B., III; Dunlap, N. K.; Sulikowski, G. A. Tetrahedron Lett. 1988, 29, 439; Maruoka, K.; Shimada, J.; Imoto, H.; Yamamoto, H. Synlett 1994, 519 and references therein.
23. Tanaka, T.; Kurozumi, S.; Toru, T.; Miura, S.; Kobayashi, M.; Ishimoto, S. Tetrahedron 1976, 32, 1713.
24. Hashimoto, S.; Watanabe, N.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1992, 1508; idem Tetrahedron Lett. 1992, 33, 2709.
25. Hashimoto, S.; Watanabe, N.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1992, 1508; idem Tetrahedron Lett. 1992, 33, 2709.
26. 1H NMR data of H-1 and H-3 protons of 2a-e 2 H-1 H-3 a 3.13 (d, J = 12.2 Hz) 4.33 (t, J = 3.9 Hz) b 3.28 (d, J = 12.2 Hz) 4.44 (dd, J = 5.8 and 2.7 Hz) c 3.14 (d, J = 12.0 Hz) 4.43 (t, J = 3.6 Hz) d 3.15 (d, J = 12.0 Hz) 4.43 (t, J = 3.7 Hz) e 3.16 (d, J = 11.5 Hz) 4.51 (t, J = 3.6 Hz)
27. Taber, D. F.; Ruckle, R. E., Jr. Tetrahedron Lett. 1985, 26, 3059.
28. Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958; Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547; Taber, D. F.; Song, Y. J. Org. Chem. 1996, 61, 6706.
29. Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958; Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547; Taber, D. F.; Song, Y. J. Org. Chem. 1996, 61, 6706.
30. Doyle, M. P.; Westrum, L. J.; Wolthuis, W. N. E.; See, M. M.; Boone, W. P.; Bagheri, V.; Pearson, M. M. J. Am. Chem. Soc. 1993, 115, 958; Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547; Taber, D. F.; Song, Y. J. Org. Chem. 1996, 61, 6706.
31. Gorthey, L. A.; Vairamani, M.; Djerassi, C. J. Org. Chem. 1985, 50, 4173; Nagao, Y.; Goto, M.; Ochiai, M.; Shiro, M. Chem. Lett. 1990, 1503; Nagao, Y.; Goto, M. Heterocycles 1995, 41, 883; Eliel, E. L.; Satici, H. J. Org. Chem. 1994, 59, 688.
32. Gorthey, L. A.; Vairamani, M.; Djerassi, C. J. Org. Chem. 1985, 50, 4173; Nagao, Y.; Goto, M.; Ochiai, M.; Shiro, M. Chem. Lett. 1990, 1503; Nagao, Y.; Goto, M. Heterocycles 1995, 41, 883; Eliel, E. L.; Satici, H. J. Org. Chem. 1994, 59, 688.
33. Gorthey, L. A.; Vairamani, M.; Djerassi, C. J. Org. Chem. 1985, 50, 4173; Nagao, Y.; Goto, M.; Ochiai, M.; Shiro, M. Chem. Lett. 1990, 1503; Nagao, Y.; Goto, M. Heterocycles 1995, 41, 883; Eliel, E. L.; Satici, H. J. Org. Chem. 1994, 59, 688.
34. Gorthey, L. A.; Vairamani, M.; Djerassi, C. J. Org. Chem. 1985, 50, 4173; Nagao, Y.; Goto, M.; Ochiai, M.; Shiro, M. Chem. Lett. 1990, 1503; Nagao, Y.; Goto, M. Heterocycles 1995, 41, 883; Eliel, E. L.; Satici, H. J. Org. Chem. 1994, 59, 688.
35. Izawa,T.; Mukaiyama, T. Chem. Lett. 1975, 161.
36. Regitz, M.; Hocker, J.; Liedhegener, A. In Organic Syntheses, Collect. Vol. V; John-Wiley & Sons: New York, 1973; p 179.