Amination of α,β-unsaturated (2-trimethylsilanylmethyl) carboxylic esters

The reactions of (2-trimethylsilanylmethyl) α,β-unsaturated carboxylic ethyl esters with NsONHCO2Et and CaO produce, after treatment with AcOH, α-methylene N-(ethoxycarbonyl) β-amino carboxylic esters through ring opening and elimination of the trimethylsilyl group from the intermediate aziridine. By ozonization and subsequent reductive cleavage these products give the corresponding N-(ethoxycarbonyl) β-amino α-hydroxy esters.