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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1071-1077

Asymmetric epoxidation of olefins catalyzed by Ti(salan) complexes using aqueous hydrogen peroxide as the oxidant

Kazuhiro Matsumoto, Yuji Sawada and Tsutomu Katsuki

Department of Chemistry, Faculty of Science, Graduate School, Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

Abstract: Ti(salan) complexes were found to be efficient catalysts for asymmetric epoxidation with aqueous hydrogen peroxide as the oxidant. In the presence of pH 7.4 phosphate buffer, the reaction of various conjugate olefins proceeded smoothly to afford the corresponding epoxides in high yield with high enantioselectivity, even on a multigram scale. Ti(salan) complexes could be prepared from Ti(OiPr)4 and the corresponding salan ligand and directly used without isolation and purification.