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The efficient azidation of beta-keto esters and silyl enol ethers using a benziodoxole-derived azide transfer reagent is reported. The azidation of cyclic beta-keto esters could be achieved in up to quantitative yields in the absence of any catalyst. In the case of less reactive linear beta-keto esters and silyl enol ethers, complete conversion and good yields could be obtained by using a zinc catalyst.
Jörg Hülsken, Pierre Vincent Dessen, Laurent Nam Ky Beziaud