Highly stereoselective indium trichloride-catalysed asymmetric aldol reaction of formaldehyde and a glucose-derived silyl enol ether in water

Abstract

The yield and stereochemical outcome of the reaction between D-glucose-derived silyl enol ether 1 (Z and E isomers) and commercial formaldehyde in water catalysed by indium(III) choride was studied.

References

1. C. J. Li, Chem. Rev., 1993, 93, 2023.
2. A. Dondoni and A. Marra, in Preparative Carbohydrate Chemistry, ed. S. Hanessian, Marcel Dekker, New York, 1997, p. 173.
3. S. Kobayashi and I. Hachiya, J. Org. Chem., 1994, 59, 3590.
4. T. P. Loh, J. Pei and G. Q. Cao, Chem. Commun., 1996, 1819.
5. D. A. Evans, in Asymmetric Synthesis, Vol. 3, Part B, ed. J. D. Morrison, Academic Press, New York, 1984, 12.
6. M. E. Garst, J. N. Bonfiglio, D. A. Grudoski and J. Marks, J. Org. Chem., 1980, 45, 2307.
7. W. J. Hehre, L. Radom, P. V. R. Schleyer and J. A. Pople, Ab Initio Molecular Theory, Wiley: New York, 1986.
8. Calculations were performed using the GAUSSIAN 92/DFT program: M. J. Frisch, G. W. Tucks, H. B. Schlegel, P. M. Gill, B. G. Johnson, M. W. Wong, J. B. Foresman, M. A. Robb, M. Head-Gordon, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, D. J. Fox, D. J. DeFrees, J. Baker, J. J. P. Stewart and J. A. Pople, GAUSSIAN 92/DFT, Gaussian Inc., Pittsburgh PA, 1992.