Iron-Catalyzed Ring-Opening Reactions of Cyclopropanols with Alkenes and TBHP: Synthesis of 5-Oxo Peroxides.

Abstract

The ring opening of cyclopropanols is rarely used in multicomponent reactions. Herein we report the three-component reaction of cyclopropanols with alkenes and tert-butyl hydroperoxide (TBHP) catalyzed by an iron catalyst. This protocol enables the incorporation of both the β-carbonyl fragment and a peroxy unit across the C═C double bond regioselectively, thus allowing an efficient, facile access to 5-oxo peroxides. Modification of the biologically active molecules and various downstream derivatizations of the peroxides are also demonstrated.