Addition of Silyl- and Stannyl Anions to Carbohydrate-Derived 2,3-Dihydro-4H-pyran-4-ones: Facile Access to Glycosyl Silanes and -Stannanes

Synlett

Volumn 1996, Issue 8, 1996, Pages 772-774

  Kirschning, Andreas ^a   Harders, Jan ^a  

^a CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012996706     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5513     Document Type: Article

References (37)

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17. 2,3-Dihydro-4H-pyran-4-ones 2-5, and 10 were synthesized according to: (a) Kirschning, A., J. Org. Chem. 1995, 60, 1228-1232. (b) Kirschning, A.; Dräger, G.; Harders, J., Synlett 1993, 289-290.
18. 2,3-Dihydro-4H-pyran-4-ones 2-5, and 10 were synthesized according to: (a) Kirschning, A., J. Org. Chem. 1995, 60, 1228-1232. (b) Kirschning, A.; Dräger, G.; Harders, J., Synlett 1993, 289-290.
19. For conjugate addition of organocopper reagents to 2,3-dihydro-4H-pyran-4-ones see: (a) Goodwin, T. E.; Rothman, N. M.; Salazar, K. L.; Shannon, L. S., J. Org. Chem. 1992, 57, 2469-2471. (b) Belllosta, V.; Czernecki, S., Carbohydr. Res. 1987, 171, 279-288. (c) Goodwin, T. E.; Crowder, C. M.; White, R. B.; Swanson, J. S.; Evans, F. E.; Meyer, W. L., J. Org. Chem. 1983, 48, 376-380. (d) Yunker; M. B.; Plaumann, D. E.; Fraser-Reid, B., Can. J. Chem. 1977, 55, 4002
20. For conjugate addition of organocopper reagents to 2,3-dihydro-4H-pyran-4-ones see: (a) Goodwin, T. E.; Rothman, N. M.; Salazar, K. L.; Shannon, L. S., J. Org. Chem. 1992, 57, 2469-2471. (b) Belllosta, V.; Czernecki, S., Carbohydr. Res. 1987, 171, 279-288. (c) Goodwin, T. E.; Crowder, C. M.; White, R. B.; Swanson, J. S.; Evans, F. E.; Meyer, W. L., J. Org. Chem. 1983, 48, 376-380. (d) Yunker; M. B.; Plaumann, D. E.; Fraser-Reid, B., Can. J. Chem. 1977, 55, 4002
21. For conjugate addition of organocopper reagents to 2,3-dihydro-4H-pyran-4-ones see: (a) Goodwin, T. E.; Rothman, N. M.; Salazar, K. L.; Shannon, L. S., J. Org. Chem. 1992, 57, 2469-2471. (b) Belllosta, V.; Czernecki, S., Carbohydr. Res. 1987, 171, 279-288. (c) Goodwin, T. E.; Crowder, C. M.; White, R. B.; Swanson, J. S.; Evans, F. E.; Meyer, W. L., J. Org. Chem. 1983, 48, 376-380. (d) Yunker; M. B.; Plaumann, D. E.; Fraser-Reid, B., Can. J. Chem. 1977, 55, 4002
22. For conjugate addition of organocopper reagents to 2,3-dihydro-4H-pyran-4-ones see: (a) Goodwin, T. E.; Rothman, N. M.; Salazar, K. L.; Shannon, L. S., J. Org. Chem. 1992, 57, 2469-2471. (b) Belllosta, V.; Czernecki, S., Carbohydr. Res. 1987, 171, 279-288. (c) Goodwin, T. E.; Crowder, C. M.; White, R. B.; Swanson, J. S.; Evans, F. E.; Meyer, W. L., J. Org. Chem. 1983, 48, 376-380. (d) Yunker; M. B.; Plaumann, D. E.; Fraser-Reid, B., Can. J. Chem. 1977, 55, 4002
23. (a) Goddard, R.; Krüger, C.; Ramadan, N. A.; Ritter, A., Angew. Chem. 1995, 107, 1107-1109; Angew. Chem. Int. Ed. Engl. 1995, 34, 1030-1032.
24. (a) Goddard, R.; Krüger, C.; Ramadan, N. A.; Ritter, A., Angew. Chem. 1995, 107, 1107-1109; Angew. Chem. Int. Ed. Engl. 1995, 34, 1030-1032.
25. (b) Fleming, I.; Newton, T. W., J. Chem. Soc., Perkin Trans. I 1984, 1805-1808.
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29. 3):δ 206.1, 83.4, 75.3, 67.4, 60.4, 46.1, 29.0, 27.4, 25.7, 18.3, 13.3, 8.7, 6.7, 4.7, -5.3, -5.8.
30. 2CuLi 1a and MeLi. Otherwise, direct methylation of the keto group in 2,3-dihydro-4H-pyran-4-ones also occurred.
31. (a) Sato, T.; Watanabe, M.; Onoda, Y.; Murayama, E., J. Org. Chem. 1988, 53, 1894-1899.
32. (b) Still, W. C., J. Am. Chem. Soc. 1978, 100, 1481-1487.
33. (c) Seebach, D.; Bürstinghaus, R.; Gröbel, B.-T.; Kolb, M., Liebigs Ann. Chem. 1977, 830-845.
34. Due to fragmentation of the intermediate enolates, reduced yields were observed when the temperature was raised above -30°C.
35. Sawyer, J. C.; Kucerovy, A.; Macdonald, T. L.; McGarvey, G. J., J. Am. Chem. Soc. 1988, 110, 842-853.
36. Configurational and conformational aspects of 1-substituted 3-uloses have been discussed in great detail by Goodwin (ref. 8a,c) and by Paulsen, H.; Bünsch, H., Chem. Ber. 1978, 111, 3484-3496.
37. Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J., J. Chem. Soc., Perkin Trans. I 1995, 317-337.