Preparation of α-functionalized alkenylmagnesium reagents via a halide–magnesium exchange

Abstract

A general preparation of alkenylmagnesium derivatives bearing an electron-withdrawing function in the α-position (Y=CN, CO 2R, CONR 2, SO 2Ph) has been made possible by using a low temperature (−40 to −30°C) bromine–magnesium exchange with i-PrMgBr in THF. This reaction has also been used to prepare 5-magnesiated-1,3-dioxin-4-one derivatives bearing an alkoxy substituent in β-position to the carbon–magnesium bond.