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Remarkable effect of tris(4-fluorophenyl)phosphine oxide on the stabilization of chiral lanthanum complex catalysts. A new and practical protocol for the highly enantioselective epoxidation of conjugated enones

Rie Kino, Kazuhiro Daikai, Toshio Kawanami, Hiroshi Furuno and Junji Inanaga*

*Institute for Materials Chemistry and Engineering, Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan, Email: inanagams.ifoc.kyushu-u.ac.jp

R. Kino, K. Daikai, T. Kawanami, H. Furuno, J. Inanaga, Org. Biomol. Chem., 2004, 2, 1822-1824.

DOI: 10.1039/b405882h (free Supporting Information)


Abstract

A new and efficient chiral catalyst system, lanthanum-chiral BINOL-tris(4-fluorophenyl)phosphine oxide-cumene hydroperoxide, was developed for the epoxidation of α,β-unsaturated ketones, thus providing the corresponding epoxy ketones with excellent enantioselectivities (up to >99% ee) in good to excellent yields at room temperature.

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Key Words

Epoxidation, Epoxy Ketones, Cumene Hydroperoxide


ID: J52-Y2004-760