Stereospecific generation of α- and β-glycosyl-lithium reagents from Glycosyl-stannanes: A stereocontrolled route to α- and β-C-glycosides

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 13, 1985, Pages 894-895

  Lesimple, Patrick ^a   Beau, Jean Marie ^a   Sinaÿ, Pierre ^a  

^a UER de Sciences Fondamentales et Appliquées ^*  (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049097590     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39850000894     Document Type: Article

References (9)

1. E.-I. Negishi in ‘Organometallics in Organic Synthesis,’ vol. 1, Wiley, New York, 1980, ch. 6, p. 394.
2. E. J. Corey and T. H. Eckrich, Tetrahedron Lett., 1984, 25, 2415.
3. W. C. Still and C. Szeekumar, J. Am. Chem. Soc., 1980, 102, 1201.
4. J.-M. Lancelin, L. Morin-Allory, and P. Sinaÿ, J. Chem. Soc., Chem. Commun., 1984, 355.
5. Tri-n-butylstannyi-lithium was prepared by the addition of n-butyl- lithium to commercial hexabutylditin in tetrahydrofuran (0 °C, 15 min), according to W. C. Still, J. Am. Chem. Soc., 1977, 99, 4836.
6. Tri-n-butylstannyi-lithium was prepared by the addition of n-butyl- lithium to commercial hexabutylditin in tetrahydrofuran (0 °C, 15 min), according to W. C. Still, J. Am. Chem. Soc., 1978, 100, 1481.
7. The equatorial organolithium derivative (4) is stabilized by a strong stereoelectronic orientational effect, see; J.-M. Lehn and G. Wipff, J. Am. Chem. Soc., 1976, 98, 7498.
8. and references cited; N. D. Epiotis, R. L. Yates, F. Bernardi, and S. Wolfe, J. Am. Chem. Soc., 1976, 98, 5435.
9. T. Cohen and M.-T. Lin, J. Am. Chem. Soc., 1984, 106, 1130.