Metal-Free Azidation of α-Hydroxy Esters and α-Hydroxy Ketones Using Azidotrimethylsilane

We herein report a commercially available perchloric acid catalyst capable of catalyzing the azidation of α-hydroxy esters, α-hydroxy ketones and taddols using azidotrimethylsilane in dichloromethane at room temperature. Various substituted tertiary alcohols are well tolerated in this reaction. C^α-tetrasubstituted α-amino acid derivatives were prepared by one-pot sequential azidation and hydrogenation procedure. The advantage of this newly developed method includes operational simplicity, ready availability of catalyst, scale-up ability, and also good functional group compatibility. (Figure presented.).