Preparation of vinylic sulphones by Peterson olefination using phenyl trimethylsilylmethyl sulphone

Abstract

The anion generated from phenyl trimethylsilylmethyl sulphone using butyl-lithium in dimethoxyethane, readily reacts at –78 °C with various carbonyl compounds to afford vinylic sulphones on work-up at room temperature. The reaction conditions are tolerant of a number of otherwise reactive functional groups such as silyl ethers, cyclopropanes, esters, acetals, and epoxides. In ether solvent trapping of the intermediate alkoxide was possible by acylation.