Double stereodifferentiation in the Lewis acid promoted C-glycosidation of activated glycals with chiral (E)-crotylsilanes

Tetrahedron

Volumn 53, Issue 32, 1997, Pages 10971-10982

  Panek, James S ^a   Schaus, Jennifer V ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAN DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; GLYCOSYLATION; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030798035     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00358-X     Document Type: Article

References (31)

1. Review: Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem. Int. Ed. Engl. 1996, 35, 1380-1419.
2. (a) Ferrier, R. J.; Prasad, N.; J. J. Chem. Soc. C, 1969, 570.
3. (b) Ferrier, R. J. Adv. Carbohyd. Chem. Biochem. 1969, 24, 199.
4. (a) Indanomycin: Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089.
5. (b) Zincophorin: Danishefsky, S. J.; Selnick, H. G.; Zelle, R. E., DeNinno, M. P. J. Am. Chem. Soc. 1988, 110, 4368-4378.
6. (c) Avermectin A: Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1989, 111, 2967-2980.
7. (d) ibid. 1987, 109, 8117-8119.
8. (e) Avermectin A: Danishefsky, S. J.; Selnick, H. G.; Armistead, D. M.; Wincott, F. E. ibid. 1987, 109, 8119-8120.
9. (a) Panek, J. S.; Yang, M. J. Am. Chem. Soc. 1991, 113, 6594-6600.
10. (b) Panek, J. S.; Yang, M. J. Org. Chem. 1991, 56, 5755-5758.
11. (a) Hayashi, T.; Konishi, M.; Ito, H.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4962-4963.
12. (b) Hayashi, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4963-4965.
13. (c) Wetter, H.; Scherer, P.; Schweizer, W. B. Helv. Chim. Acta 1979, 62, 1985-1989.
14. (d) Wetter, H.; Scherer, P. Helv. Chim. Acta 1983, 66, 118-122.
15. (a) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316.
16. (b) Matassa, V. G.; Jenkins, P. R.; Kumin, A.; Damm, L.; Schreiber, J.; Felix, D.; Zass, E.; Eschenmoser, A. Israel. J. Chem. 1989, 29, 321-343.
17. (c) The precise contribution of steric and electronic effects of the silyl group of the (E)-crotylsilane to the stereoselectivity of the reaction either in its transition state structure or the ground state are, of course, not known. However, for allylsilanes the conformational requirements seem to be well defined; for maximum stabilization of the carbocation β to the silicon group it is necessary for the C-Si bond to be oriented antiperiplanar to the emerging empty p-orbital (see Fleming, I. Org. React. 1989, 37, 57).
18. (a) Heathcock, C. H. In Comprehensive Organic Synthesis, Vol. II; Heathcock, C. H. Ed. Pergamon press; Oxford, 1991; chapter 1.6.
19. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
20. (c) Double stereodifferentiating reactions: Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-31.
21. Roush, R. W. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon: Oxford, 1990; Vol. 2, p 1-53.
22. Lipase Amano A. K. was purchased from Amano International Enzyme Co. Inc., VI, U. S. A.
23. Sparks, M. A.; Panek, J. S. J. Org. Chem. 1991, 56, 3431-3438.
24. Panek, J. S; Yang, M. J. Am. Chem. Soc. 1991, 113, 6594-6600.
25. For recent reviews on the chemistry of allylmetals see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2239.
26. (b) Fleming, I. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon Press: Oxford 1979; Vol. 3, p 539.
27. (c) Chan, T. H.; Wang, D. Chem. Rev. 1992, 92, 995.
28. Panek, J. S.; Jain, N. J. Org. Chem. 1994, 59, 2674-2675.
29. Danishefsky, S. J.; DeNinno, S.; Lartey, P.; J. Am. Chem. Soc. 1987, 109, 2082-2089.
30. Panek, J. S.; Beresis, R. T; Celatka, C. A. J. Org. Chem. 1996, 61, 6494-6495.
31. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.