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Org Biomol Chem. 2004 Jul 07;2(13):1822-4. doi: 10.1039/b405882h. Epub 2004 Jun 04.

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.

Organic & biomolecular chemistry

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

Affiliations

  1. Institute for Materials Chemistry and Engineering, Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan.

PMID: 15227531 DOI: 10.1039/b405882h

Abstract

A new and efficient chiral catalyst system, lanthanum-chiral BINOL-tris(4-fluorophenyl)phosphine oxide-cumene hydroperoxide, was developed for the epoxidation of alpha, beta-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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