Facial selectivity in the cycloaddition of heterodienes to carbohydrate cyclic ketene acetals. A novel synthesis of disaccharide derivatives

Abstract

Carbohydrate ketene acetals derived from mannopyranose and glucopyranose are shown to serve as electron-rich dienophiles in facially selective, Lewis acid-catalyzed inverse electron demand hetero-Diels–Alder reactions.

References

1. G. Desimoni and G. Tacconi, Chem. Rev., 1975, 75, 651; For applications to carbohydrates, see S. David, A. Lubineau and A. Thieffry, Tetrahedron, 1978, 34, 299 and S. David, J. Eustache and A. Lubineau, J. Chem. Soc., Perkin Trans. I, 1979, 1795.
2. D. L. Boger and S. M. Weinreb, Hetero-Diels–Alder Methodology in Organic Synthesis, Academic Press, San Diego, 1987.
3. See, e.g. R. R. Schmidt, Acc. Chem. Res., 1986, 19, 250 and references cited therein.
4. L. F. Tietze and E. Voss, Tetrahedron Lett., 1986, 27, 6181.
5. M. L. Sznaidman, S. C. Johnson, C. Crasto and S. M. Hecht, J. Org. Chem., 1995, 60, 3942.
6. For examples of the use of lanthanide catalysts in Diels–Alder reactions, see M. Bednarski and S. Danishefsky, J. Am. Chem. Soc., 1983, 105, 3716.
7. The enhanced reactivity of 1vs. 2 with acrolein could involve better coordination of the oxyphilic Yb³⁺ catalyst with the dienophile, thereby allowing for better stabilization of the HOMO_dienophile and a lower energy transition state. See J. Sauer and R. Sustmann, Angew. Chem. Int. Ed. Engl., 1980, 19, 779.
8. D. L. Boger and K. D. Robarge, J. Org. Chem., 1988, 53, 3373.
9. L. F. Tietze, C. Schneider and A. Montenbruck, Angew. Chem., Int. Ed. Engl., 1994, 33, 980.
10. D. A. Evans, M. D. Ennis and D. J. Mathre, J. Am. Chem. Soc., 1982, 104, 1737.
11. W. Oppolzer, C. Chapuis and G. Bernardinelli, Helv. Chim. Acta, 1984, 67, 1397.
12. W.-C. Chou, L. Chen, J.-M. Fang and C.-H. Wong, J. Am. Chem. Soc., 1994, 116, 6191.
13. For reference to the use of chiral dienophiles in diastereofacially selective [4 + 2] cycloadditions, see W. Choy, L. A. Reed, III and S. Masamune, J. Org. Chem., 1983, 48, 1139.
14. For examples of the regio- and stereo-selective reduction of orthoesters with hydrides, see E. Eliel and F. W. Nader, J. Am. Chem. Soc., 1970, 92, 3045; G. Stork and S. D. Rychnovsky, J. Am. Chem. Soc., 1987, 109, 1565.