In situ generation of Mes2Mg as a non-nucleophilic carbon-centred base reagent for the efficient one-pot conversion of ketones to silyl enol ethers.

William J Kerr, Allan J B Watson, Douglas Hayes

Index: Org. Biomol. Chem. 6(7) , 1238-43, (2008)

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Abstract

Treatment of commercially available MesMgBr with 1,4-dioxane produces the key Mes(2)Mg reagent in situ which then mediates the deprotonation of ketones to deliver trimethylsilyl enol ethers, at readily accessible temperatures and without any nucleophilic addition, in an expedient and high yielding one-pot process.