Oxidative addition of azide anion to triisopropylsilyl enol ethers: Synthesis of α-azido ketones and 2-amino(methoxycarbonyl)alk-2-en-1-ones

Article abstract of DOI:10.1016/0040-4020(95)00681-W

Treatment of triisopropylsilyl enol ethers with ceric ammonium nitrate/sodium azide at -20°C in acetonitrile gives α-azido ketones in average to good yields (50-80%). Subsequent conversion of the α-azido ketones into 2-amino(methoxycarbonyl)cycloalk-2-en-1-ones is described.