Novel Oxidative Synthetic Transformations Driven by Chiral Oxoammmonium Salts

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Novel synthetic use of azaadamantane-type oxoammonium salts has been exploited. It was found that 9-nor-azaadamantane N-oxy (Nor-AZADO) gives the corresponding oxoammonium salts that exhibit superior activities to AZADO derived oxoammonium salts. Several novel oxidative transformations using Nor-AZADO have been developed including (1) silyl enol ethers to a,b-unsaturated ketones and (2) silyl enol ethers to 1,2-diketones.