Silver(I)-catalyzed addition of zirconocenes to glycal epoxides. A new synthesis of α-c-Glycosides

Organic Letters

Volumn 7, Issue 3, 2005, Pages 483-485

  Wipf, Peter ^a   Pierce, Joshua G ^a   Zhuang, Nian ^a,b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; EPOXIDE; GLYCOSIDE; SILVER DERIVATIVE; ZIRCONOCENE;

ARTICLE; CATALYSIS; SYNTHESIS;

CATALYSIS; EPOXY COMPOUNDS; GLYCOSIDES; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; SILVER; STEREOISOMERISM; ZIRCONIUM;

EID: 13844271406     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0475414     Document Type: Article

References (49)

1. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913.
2. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432.
3. Yang, G.; Schmieg, J.; Tusji, M.; Franck, R. W. Angew. Chem., Int. Ed. 2004, 43, 3818.
4. (a) McGarvey, G. J.; Schmidtmann, F. W.; Benedum, T. E.; Kizer, D. E. Tetrahedron Lett. 2003, 44, 3775.
5. (b) Harvey, J. E.; Raw, S. A.; Taylor, R. J. K. Org. Lett. 2004, 6, 2611.
6. (c) Ben, A.; Yamauchi, T.; Matsumoto, T.; Suzuki, K. Synlett 2004, 225.
7. (d) Gardiner, J. M.; Mills, R.; Fessard, T. Tetrahedron Lett. 2004, 45, 1215.
8. (e) Terauchi, M.; Abe, H.; Matsuda, A.; Shuto, S. Org. Lett. 2004, 6, 3751.
9. (f) Steinhuebel, D. P.; Fleming, J. J.; Du Bois, J. Org. Lett. 2002, 4, 293.
10. (g) Vakalopoulos, A.; Hoffmann, H. M. R. Org. Lett. 2001, 3, 177.
11. Zhuang, N. MS Thesis, University of Pittsburgh, 1997.
12. (a) Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. J. Am. Chem. Soc. 2001, 123, 9545.
13. (b) Parrish, J. D.; Little, R. D. Org. Lett. 2002, 4, 1439.
14. (a) Grotenbreg, G. M.; Tuin, A. W.; Witte, M. D.; Leeuwenburgh, M. A.; Van Boom, J. H.; Van der Marel, G. A.; Overkleeft, H. S.; Overhand, M. Synlett 2004, 904.
15. (b) Xue, S.; Han, K.-Z.; He, L.; Guo, Q.-X. Synlett 2003, 870.
16. (c) Leeuwenburgh, M. A.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H. J. Carbohydr. Chem. 2003, 22, 549.
17. (d) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281.
18. (e) Allwein, S. P.; Cox, J. M.; Howard, B. E.; Johnson, H. W. B.; Rainier, J. D. Tetrahedron 2002, 58, 1997.
19. (f) Bailey, J. M.; Craig, D.; Gallagher, P. T. Synlett 1999, 132.
20. (g) Rainier, J. D.; Allwein, S. P. J. Org. Chem. 1998, 63, 5310.
21. (h) Evans, D. A.; Trotter, B. W.; Cote, B. Tetrahedron Lett. 1998, 39, 1709.
22. (i) Manabe, S.; Ito, Y.; Ogawa, T. Chem. Lett. 1998, 919.
23. (j) Leeuwenburgh, M. A.; Timmers, C. M.; van der Marel, G. A.; van Boom, J. H.; Mallet, J.-M.; Sinay, P. G. Tetrahedron Lett. 1997, 38, 6251.
24. (k) Best, W. M.; Ferro, V.; Harle, J.; Stick, R. V.; Tilbrook, D. M. G. Aust. J. Chem. 1997, 50, 463.
25. (l) Bellosta, V.; Czernecki, S. J. Chem. Soc., Chem. Commun. 1989, 199.
26. Klein, L. L.; McWhorter, W. W., Jr.; Ko, S. S.; Pfaff, K. P.; Kishi, Y.; Uemura, D.; Hirata, Y. J. Am. Chem. Soc. 1982, 104, 7362.
27. (a) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
28. (b) Wipf, P.; Kendall, C. Top. Organomet. Chem. 2004, 8, 1.
29. Wipf, P.; Nunes, R. L. Tetrahedron 2004, 60, 1269.
30. Glycal epoxides were prepared by Danishefsky's protocol: (a) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661. (b) Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
31. Glycal epoxides were prepared by Danishefsky's protocol: (a) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661. (b) Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
32. (a) Wipf, P.; Xu, W. J. Org. Chem. 1993, 58, 825.
33. (b) Wipf, P.; Xu, W. Tetrahedron 1995, 51, 4551.
34. (c) Wipf, P.; Xu, W.; Kim, H.; Takahashi, H. Tetrahedron 1997, 53, 16575.
35. (d) Wipf, P.; Methot, J.-L. Org. Lett. 1999, 1, 1253.
36. 4 system for glycosyl transfer reactions of anomeric sulfoxides, see: Wipf, P.; Reeves, J. T. J. Org. Chem. 2001, 66, 7910.
37. Use of 1 equiv of silver perchlorate on Celite led to a fast conversion to give 4 in 85% yield.
38. (a) Maeta, H.; Hashimoto, T.; Hasegawa, T.; Suzuki, K. Tetrahedron Lett. 1992, 33, 5965.
39. (b) Ohmori, K.; Hatakeyama, K.; Ohrui, H.; Suzuki, K. Tetrahedron 2004, 60, 1365.
40. (a) Bhagwatheeswaran, H.; Gaur, S. P.; Jain, P. C. Synthesis 1976, 615.
41. (b) Ramage, R.; Hopton, D.; Parrott, M. J.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. 1 1984, 1357.
42. (c) Desai, M. C.; Thadeio, P. F.; Lefkowitz, S. L. Tetrahedron Lett. 1993, 34, 5831.
43. 2 (8:2, EtOAc:hexanes) to yield 39 mg (76%) of 4 as a colorless oil.
44. In all reactions, a minor side product was derived from decomposition of the glycal epoxide under the Lewis acidic conditions. At lower temperatures (0°C), the conversion was similar, but the side product was also formed to a comparable extent.
45. Both 4-octyne and 6-dodecyne were used under the typical reaction conditions, but no significant product formation was observed. The reaction with these substrates was not further optimized.
46. Deactivating carbohydrate protecting groups such as acetates have proven unsatisfactory in previous work with glycal epoxides and were not explored in the present studies; see refs 10 and 71.
47. (a) Durrat, F.; Xie, J.; Valery, J.-M. Tetrahedron Lett. 2004, 45, 1477.
48. (b) Caputo, R.; Festa, P.; Guaragna, A.; Palumbo, G.; Pedatella, S. Carbohydr. Res. 2003, 338, 1877.
49. (c) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2001, 2380.