2-Substituted-2,4-endo-dimethyl-8-oxabicyclo[3.2.1]octan-3-ones as catalysts for the asymmetric epoxidation of some alkenes with Oxone®

Abstract

A range of 2-substituted-2,4-dimethyl-8-oxabicyclo[3.2.1]octan-3-ones 13–18 are available in four steps and in states of high optical purity. The fluoroketone 18 was shown to be a catalyst for the asymmetric epoxidation of stilbene, (E)-methylstilbene, phenylstilbene and chalcone (59–68% ee at 24–67% conversion) using Oxone^® as the primary oxidant.