Abstract
Silica-supported chiral tantalum alkoxides are active catalysts for the asymmetric epoxidation of propenol and trans hex-2-en-1ol. The influence of different parameters on their catalytic performance was followed: the impregnation duration by a tartrate (step in their preparation); the nature of the solvent (CH2Cl2, pentane, toluene) and of the oxidant (TBHP, CHP, H2O2); poisoning effects by water or t-butanol; the reaction temperature and the substrate concentration.
Similar content being viewed by others
References
D. Meunier, A. Piechaczyk, A. de Mallmann and J.M. Basset, Angew. Chem., Int. Ed. Eng. 38 (1999) 3540.
T. Katsuki and K.B. Sharpless, J. Am. Chem. Soc. 102 (1980) 5974.
T. Katsuki and K.B. Sharpless, US Patent 4,471,130 (1984).
R.M. Hanson and K.B. Sharpless, J. Org. Chem. 51 (1986) 1922.
Y. Gao, M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune and K.B. Sharpless, J. Am. Chem. Soc. 109 (1987) 5765.
K. Karjalaien, O.E.O. Hormi and D.C. Sherrington, Tetrahedron: Asymmetry 9 (1998) 1563.
M.J. Farrall, M. Alexis and M. Tecarten, Nouv. J. Chim. 7 (1983) 449.
S. Xiang, Y. Zhang, Q. Xin and C. Li, Angew. Chem., Int. Ed. 41 (2002) 821.
M. Dusi, T. Mallat and A. Baiker, Catal. Rev.—Sci. Eng. 42 (2000) 213.
G.J. Hutchings, D.F. Lee and A.R. Minihan, Catal. Lett. 33 (1995) 369.
C. Cativiela, J.M. Fraile, J.I. Garcia and J.A. Mayoral, J. Mol. Catal., A112 (1996) 259.
M.G. Finn and K.B. Sharpless, J. Am. Chem. Soc. 113 (1991) 113.
R.D. Schrock and J.D. Fellmann, J. Am. Chem. Soc. 100 (1978) 3359.
V. Dufaud, G.P. Niccolai, J. Thivolle-Cazat and J.M. Basset, J. Am. Chem. Soc. 117 (1995) 4288.
S.S. Woodard, M.G. Finn and K.B. Sharpless, J. Am. Chem. Soc. 113 (1991) 106.
M. Bulliard and W. Shum, in: Proceedings of the Chiral '95 USA Symposium (1995) p. 5.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Meunier, D., de Mallmann, A. & Basset, JM. Asymmetric Epoxidation of Allylic Alcohols Catalyzed by (≡SiO) x Ta(OEt)3-x (Dialkyl Tartrate Diolate): Influence of the Reaction Conditions. Topics in Catalysis 23, 183–189 (2003). https://doi.org/10.1023/A:1024845009125
Issue Date:
DOI: https://doi.org/10.1023/A:1024845009125