Under using anhydrous toluene as a solvent, N,N-dimethyl carbamoyl(trimethyl)silane reacted with a series of aryl ketones or unsaturated aryl ketones at 105 ℃ to afford α-siloxyamide derivatives in good yields (60%~89%). The structures of the products were characterized by element analysis, 1 H NMR, 13 C NMR and IR spectra. The alkyl ketones including the alkyl-aryl ketones and alkyl-unsaturated ketones poorly reacted with N,N-dimethylcarbamoyl(trimethyl)silane. The experimental results showed that the electronic property of the substituted group on the aryl ring strongly affected the reaction. In the case of the aryl ketones with stronger donor group on the aryl ring, the longer time was needed for the reaction.
N,N-Dimethylcarbamoyl(trimethyl)silane reacted with a series of α-ketoesters in anhydrous toluene at 60 ℃ to afford α-alkoxycarbonyl-α-siloxy amide derivatives in good yields (70%~99%). When the alkyl of α-ketoesters was L-2-isopropyl-5-methylcyclohexyl, the reactions possess stereo selectivity. The experimental results showed that the electronic property of the substituted group on the aryl ring affected both the reaction ratio and the yields of products. The structures of the products were characterized by element analysis, 1 H NMR, 13 C NMR and IR spectra. A reaction mechanism is proposed. The mild and no catalyst conditions, simple procedure, less byproducts and good yields provide an effective method for the preparation of α-alkoxycarbonyl-α-hydroxy amides.
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