Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1071-1077
doi:10.1351/pac200880051071
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.
Keywords: asymmetric synthesis; epoxide; hydrogen peroxide; oxidation; titanium.
*Paper based on a presentation at the 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), 2-6 August 2007, Nara, Japan. Other presentations are published in this issue, pp. 807-1194.
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