Stereoselective Palladium-Catalyzed O-Glycosylation Using Glycals

Journal of the American Chemical Society

Volumn 126, Issue 5, 2004, Pages 1336-1337

  Kim, Hahn ^a   Men, Hongbin ^a   Lee, Chulbom ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL; GLUCOSE DERIVATIVE; GLYCAL; GLYCOCONJUGATE; GLYCOSIDE; LEWIS ACID; MERCURY; PALLADIUM; PHOSPHINE DERIVATIVE; TRANSITION ELEMENT; UNCLASSIFIED DRUG; ZINC OXIDE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DIHYDROXYLATION; GLYCOSYLATION; HYDRATION; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY;

CATALYSIS; DISACCHARIDES; GLYCOSIDES; GLYCOSYLATION; PALLADIUM; STEREOISOMERISM;

EID: 1042288189     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039746y     Document Type: Article

References (44)

1. (a) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
2. (b) Nicolaou, K. C.; Mitchell, H. J. Angew. Chem., Int. Ed. 2001, 40, 1576.
3. (a) Ferrier, R. J. J. Chem. Soc. C 1964, 5443.
4. (b) Ferrier, R. J.; Ciment, D. M. J. Chem. Soc. C 1966, 441.
5. (c) Ferrier, R. J.; Prasad, N. J. Chem. Soc. Chem. Commun. 1968, 476.
6. (d) Ferrier, R. J.; Prasad, N. J. Chem. Soc. C 1969, 570.
7. (e) Ferrier, R. J.; Prasad, N. J. Chem. Soc. C 1969, 575.
8. (f) Ferrier, R. J. Adv. Carbohydr. Chem. Biochem. 1969, 199.
9. For reviews, see: (g) Ferrier, R. J. Top. Curr. Chem. 2001, 215, 153.
10. (h) Ferrier, R. J.; Zubkov, O. A. Org. React. 2003, 62, 569.
11. (a) Fraser-Reid, B. Acc. Chem. Res. 1975, 8, 192; 1985, 18, 347; 1996, 29, 57.
12. (a) Fraser-Reid, B. Acc. Chem. Res. 1975, 8, 192; 1985, 18, 347; 1996, 29, 57.
13. (a) Fraser-Reid, B. Acc. Chem. Res. 1975, 8, 192; 1985, 18, 347; 1996, 29, 57.
14. (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycoside; Pergamon Press: Tarrytown, NY, 1995.
15. (c) Postema. M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, FL, 1995.
16. (d) Csuk, R.; Schaade, M.; Krieger, C. Tetrahedron 1996, 52, 6397.
17. The difficulty of forming a π-allylpalladium species from a glycal system has been noted, see: (a) RajanBabu, T. V. J. Org. Chem. 1985, 50, 3642.
18. (b) Babu, R. S.; O'Doherty, G. A. J. Am. Chem. Soc. 2003, 125, 12406.
19. For recent examples of Pd-catalyzed O-glycosylation using a more activated pyranone system, see: (a) Comely, A. C.; Eelkema, R.; Minnaard, A. J. ; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 8714,
20. (b) Reference 4b.
21. Kim, H.; Lee, C. Org. Lett. 2002, 4, 4369.
22. Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
23. Fraser-Reid, B.; Wu, Z.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 1434.
24. Spijker, N. M.; van Boeckel, C. A. A. Angew. Chem., Int. Ed. Engl. 1991, 30, 180.
25. (a) Abdel-Rahman, A. A.-H.; Winterfield, G. A.; Takhi, M.; Schmidt, R. R. Eur. J. Org. Chem. 2002, 713.
26. (b) Babu, B. S.; Balasubramanian, K. K. Synth. Commun. 1999, 29, 4299.
27. (c) Grynkiewicz, G.; Priebe, W.; Zamojski, A. Carbohydr. Res. 1979, 68, 33.
28. 1H NMR analysis. See Supporting Information.
29. (a) Murphy, P. V.; O'Brien, J. L.; Smith, A. B. Carbohydr. Res. 2001, 334, 327.
30. (b) Friesen, R. W.; Danishefsky, S. J. Tetrahedron 1990, 46, 103.
31. (a) Brown, H. C.; Geoghegan, P. J. J. Am. Chem. Soc. 1967, 89, 1522.
32. (b) Brown, H. C.; Geoghegan, P. J. J. Org. Chem. 1970, 35, 1844.
33. (a) Servi, S. J. Org. Chem. 1985, 50, 5865.
34. (b) Hart, D. J.; Hong, W. P.; Hsu, L.-Y. J. Org. Chem. 1987, 52, 4665.
35. (c) Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2002, 4, 1771.
36. Path A: (a) Ferrier, R. J.; Prasad, N. J. Chem. Soc. C 1969, 581.
37. Path B: (b) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730.
38. (c) Bäckvall, J.-E.; Nordberg, R. E. J. Am. Chem. Soc. 1981, 103, 4959.
39. Path C: (d) Takahashi, T.; Jinbo, Y.; Kitamura, K.; Tsuji, J. Tetrahedron Lett. 1984, 25, 5921.
40. (e) Granberg, K. L.; Bäckvall, J.-E. J. Am. Chem. Soc. 1992, 114, 6858.
41. (f) Although Path D for a π-allylpalladium alkoxide species is unreported, the reductive elimination mechanism of an arylpalladium alkoxide species has been known. See: Widenhoefer, R. A.; Zhong, H. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787.
42. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
43. (a) Steinhuebel, D. P.; Fleming, J. J.; Du Bois, J. Org. Lett. 2002, 4, 293.
44. (b) In control experiments, both 1 and 1′ failed to undergo the O-glycosylation in the absence of a Zn(II) ion. Also see refs 4 and 5.