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

J Thibonnet, VA Vu, L Bérillon, P Knochel

Index: Thibonnet, Jerome; Anh Vu, Viet; Berillon, Laurent; Knochel, Paul Tetrahedron, 2002 , vol. 58, # 24 p. 4787 - 4799

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Citation Number: 49

Abstract

A general preparation of alkenylmagnesium derivatives bearing an electron-withdrawing function in the α-position (Y= CN, CO2R, CONR2, SO2Ph) 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.