Stereocontrolled synthesis of α-C-galactosamine derivatives promoted by samarium diiodide: An example of chelation controlled C-glycosylation

Chemical Communications

Volumn , Issue 16, 1996, Pages 1883-1884

  Urban, Dominique ^a   Skrydstrup, Troels ^a   Riche, Claude ^b   Chiaroni, Angèle ^b   Beau, Jean Marie ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003148293     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960001883     Document Type: Article

References (19)

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2. D. Mazéas, T. Skrydstrup and J.-M. Beau, Angew. Chem., Int. Ed. Engl., 1995, 34, 909; For an application of these results, see: O. Jarreton, T. Skrydstrup and J.-M. Beau, Chem. Commun., 1996, 1661.
3. For several reviews on the synthesis of C-glycosides: M. H. D. Postema, Tetrahedron, 1992, 48, 8545; J. Herscovici, K. Antonakis, in Studies in Natural Product Chemistry, Vol. 10, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1992.
4. For several reviews on the synthesis of C-glycosides: M. H. D. Postema, Tetrahedron, 1992, 48, 8545; J. Herscovici, K. Antonakis, in Studies in Natural Product Chemistry, Vol. 10, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1992.
5. For other syntheses of C-glycosyl analogues of 2-aminoglycosides not discussed in the above reviews, see: (a) M. Hoffmann and H. Kessler, Tetrahedron Lett., 1994, 35, 6067; (b) A. Wei, A. Haudrechy, C. Audin, H.-S. Jun, N. Haudrechy-Bretal and Y. Kishi, J. Org. Chem., 1995, 60, 2160; (c) E. Ayadi, S. Czernecki and J. Xie, Chem. Commun., 1996, 347; (d) L. Jobron, C. Leteux, A. Veyrières and J.-M. Beau, J. Carbohydr. Chem., 1994, 13, 507; (e) K. H. Kim and R. I. Hollingsworth, Tetrahedron Lett., 1994, 35, 1031; (f) A. Mbongo, C. Frèchou, D. Beaupère, R. Uzan and G. Demailly, Carbohydr. Res., 1993, 246, 361.
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18. 2: G. A. Molander and C. R. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, Chem. Rev., 1992, 92, 29; D. P. Curran, T. L. Fevig, C. P. Jaspersen and M. L. Totleben, Synlett, 1992, 943; H. B. Kagan and J. L. Namy, Tetrahedron, 1986, 42, 6573.
19. 2: G. A. Molander and C. R. Harris, Chem. Rev. 1996, 96, 307; G. A. Molander, Chem. Rev., 1992, 92, 29; D. P. Curran, T. L. Fevig, C. P. Jaspersen and M. L. Totleben, Synlett, 1992, 943; H. B. Kagan and J. L. Namy, Tetrahedron, 1986, 42, 6573.