Elimination reactions of glycosyl selenoxides

Tetrahedron

Volumn 60, Issue 38, 2004, Pages 8411-8419

  Chambers, David J ^a   Evans, Graham R ^b   Fairbanks, Antony J ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UCB PHARMA   (Belgium)

Author keywords

Carbohydrates; Elimination; Glycals; Oxidation; Selenoglycosides; Selenoxides

Indexed keywords

OLIGOSACCHARIDE; OXIDE;

ARTICLE; ELIMINATION REACTION; OXIDATION; PRIORITY JOURNAL; SHARPLESS EPOXIDATION;

EID: 4444332884     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.005     Document Type: Article

References (40)

1. See for example: (a) D. Kahne, S. Walker, Y. Cheng, and D. Van Engen J. Am. Chem. Soc. 111 1989 6881 6882
2. L. Yan, C.M. Taylor, R. Goodnow, and D. Kahne J. Am. Chem. Soc. 116 1994 6953 6954
3. D. Crich, and S. Sun Tetrahedron 54 1998 8321 8348
4. J. Gildersleeve, R.A. Pascal, and D. Kahne J. Am. Chem. Soc. 120 1998 5961 5969
5. J. Liu, C.-H. Huang, and C.-H. Wong Tetrahedron Lett. 43 2002 3447 3448
6. M. Tingoli, A. Temperini, L. Testaferri, M. Tiecco, and G. Resnati Carbohydr. Lett. 3 1998 39 46
7. For a review see: S.J. Danishefsky, and M.T. Bilodeau Angew. Chem., Int. Ed. Engl. 35 1996 1380 1419
8. R.J. Ferrier, and N.J. Prasad J. Chem. Soc. C 1969 570 575
9. For some recent references see: (a) N.R. Swamy, and Y. Venkateswarlu Synthesis 2002 598 600
10. M. Takhi, A.A.-H. Abdel-Rahman, and R.R. Schmidt Synlett 2001 427 429
11. C. Masson, J. Soto, and M. Bessodes Synlett 2000 1281 1282
12. H.Y. Godage, and A.J. Fairbanks Tetrahedron Lett. 41 2000 7589 7593
13. H.Y. Godage, and A.J. Fairbanks Tetrahedron Lett. 44 2003 3631 3635
14. H.Y. Godage, D.J. Chambers, G.R. Evans, and A.J. Fairbanks Org. Biomol. Chem. 1 2003 3772 3786
15. H.J. Reich Acc. Chem. Res. 12 1979 22 30
16. G. Jaurand, J.-M. Beau, and P. Sinaÿ J. Chem. Soc., Chem. Commun. 1982 701 703
17. C.E. Heath, M.C. Gillam, C.S. Callis, R.R. Patto, and C.J. Abelt Carbohydr. Res. 307 1998 371 373
18. W.-B. Yang, Y.-Y. Yang, Y.-F. Gu, S.-H. Wang, C.-C. Chang, and C.-H. Lin J. Org. Chem. 67 2002 3773 3782
19. For a synthetic route to 2-deoxy furanoid glycals via selenoxide elimination see F. Bravo, M. Kassou, Y. Díaz, and S. Castillón Carbohydr. Res. 336 2001 83 97
20. S. Mehta, and B.M. Pinto J. Org. Chem. 58 1993 3269 3276
21. R. Benhaddou, S. Czernecki, and D. Randriamandimby Synlett 1992 967 968
22. R.V. Stick, M.G. Tilbrook, and S.J. Williams Aust. J. Chem. 50 1997 233 235
23. N. Jones, D. Mundy, and R.D. Whitehouse J. Chem. Soc., Chem. Commun. 1970 86 87
24. H.J. Reich, S. Wollowitz, J.E. Trend, F. Chow, and D.F. Wendelborn J. Org. Chem. 43 1978 1697 1705
25. For a preliminary communication see: D.J. Chambers, G.R. Evans, and A.J. Fairbanks Tetrahedron Lett. 44 2003 5221 5223
26. S.C. Ennis, I. Cumpstey, A.J. Fairbanks, T.D. Butters, M. Mackeen, and M.R. Wormald Tetrahedron 58 2002 9403 9411
27. K.D. Randall, B.D. Johnston, P.N. Brown, and M.B. Pinto Carbohydr. Res. 325 2000 253 264
28. F. Micheel, F.-P. Van De Kamp, and H. Petersen Chem. Ber. 90 1957 521 526
29. D.M. Gordon, and S.J. Danishefsky Carbohydr. Res. 206 1990 361 366
30. T. Hori, and K.B. Sharpless J. Org. Chem. 43 1978 1689 1697
31. A.P. Brunetire, and J.Y. Lallemand Tetrahedron Lett. 29 1988 2179 2182
32. V.K. Aggarwal, G.R. Evans, E. Moya, and J. Dowden J. Org. Chem. 57 1992 6390 6391
33. Required to prevent side reactions caused by selenenic acids and their disproportionation products.
34. P.A. Gent, and R. Gigg J. Chem. Soc., Perkin Trans. 1 1974 1446 1455
35. These could possibly be the corresponding glycosyl selenoxide and the glycosyl selenone. One referee suggested that formation of the lactol 21, in preference to any methyl glycoside, might arise from an Se to O rearrangement to produce a glycosyl selenenate which then hydrolyses. However, we currently have no evidence to support this mechanism, and presume that the lactol may simply arise from acid catalysed decomposition of the glycosyl selenoxide on silica.
36. Our observations here are in contrast with a report on the use of glycosyl selenoxides as glycosyl donors when produced by oxaziridine oxidation of selenoglycosides. See Ref. 3.
37. U.E. Udodong, and B. Fraser-Reid J. Org. Chem. 54 1989 2103 2112
38. D. Crich, and W. Cai J. Org. Chem. 64 1999 4926 4930
39. T. Ogawa, S. Nakabayashi, and K. Sasajima Carbohydr. Res. 95 1981 308 312
40. I. Damager, C.E. Olsen, B.L. Moeller, and M.S. Motawia Carbohydr. Res. 320 1999 19 30