Methyl 2,3,4-Tri-O-benzyl-α-D-glucopyranosyl-derived γ-silyloxy allylic stannanes as reagents for SE2′ additions to aldehydes

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4611-4616

  Marshall, James A ^a   Elliott, L Michelle ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000516883     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9601627     Document Type: Article

References (28)

1. For recent reviews, see (a) Marshall, J. A. Chemtracts-Org. Chem. 1992, 5, 75. (b) Marshall, J. A. Chem. Rev. 1996, 96, 31.
2. For recent reviews, see (a) Marshall, J. A. Chemtracts-Org. Chem. 1992, 5, 75. (b) Marshall, J. A. Chem. Rev. 1996, 96, 31.
3. (a) Marshall, J. A.; Beaudoin, S.; Lewinski, K. J. Org. Chem. 1993, 58, 5876.
4. (b) Marshall, J. A.; Seletsky, B. M.; Luke G. P. J. Org. Chem. 1994, 59, 3413.
5. (c) Marshall, J. A.; Beaudoin, S. J. Org. Chem. 1994, 59, 6614.
6. (d) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 105.
7. (e) Marshall, J. A.; Beaudoin, S. J. Org. Chem. 1996, 61, 581.
8. For possible applications, see Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743.
9. Jarosz, S.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 4011. For a related approach to disaccharides, see Roush, W. R.; VanNieuwenhze, M. S. J. Am. Chem. Soc. 1994, 116, 8536.
10. Jarosz, S.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 4011. For a related approach to disaccharides, see Roush, W. R.; VanNieuwenhze, M. S. J. Am. Chem. Soc. 1994, 116, 8536.
11. Marshall, J. A.; Welmaker, G. S. J. Org. Chem. 1992, 57, 7158.
12. Marshall, J. A; Jablonowski, J. A.; Luke, G. P. J. Org. Chem. 1994, 59, 7825.
13. At this point the configuration was not known. For clarity of the discussion we will show the configurations that were later proved.
14. 5
15. To achieve economy of the space the adducts are shown in a hairpin projection rather than the usual zig-zag arrangement. It is the latter form from which the terms "syn" and "anti" are derived. We apologize for any confusion resulting from this presentation.
16. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920. We are indebted to Albert Garofalo for a sample of this material.
17. Veysoglu, T.; Mitscher, L. A.; Swayze, J. K. Synthesis 1980, 807.
18. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370.
19. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
20. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
21. Marshall, J. A.; Jablonowski, J. A.; Elliott, L. M. J. Org. Chem. 1995, 60, 2662.
22. Fortes, C. C.; Garrote, C. F. D. Synth. Commun. 1993, 23, 2869.
23. Yamamoto, Y.; Yatagai, H.; Ishihara, Y.; Norihika, M.; Maruyama, K. Tetrahedron 1984, 40, 2239. For a recent review, see Yamamoto, Y.; Shida, N. Advances in Detailed Reaction Mechanisms; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 1-44.
24. Yamamoto, Y.; Yatagai, H.; Ishihara, Y.; Norihika, M.; Maruyama, K. Tetrahedron 1984, 40, 2239. For a recent review, see Yamamoto, Y.; Shida, N. Advances in Detailed Reaction Mechanisms; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 1-44.
25. 14
26. Marshall, J. A.; Jablonowski, J. A.; Welmaker, G. S. J. Org. Chem. 1996, 61, 2904.
27. For a preliminary disclosure of some of these results, see ref 14.
28. For typical experimental protocols, see Marshall, J. A.; Wang, X-j. J. Org. Chem. 1991, 56, 960.