Preparation of α-(N-trimethylsilyl)imino esters and their use in the synthesis of α-amino esters and 2-alkoxycarbonylimidazol-4(2H)-ones

Abstract

The reaction of α-keto esters with lithium 1,1,1,3,3,3-hexamethyldisilazanide afforded α-(N-trimethylsilyl)imino esters in good yields, which were reduced to the corresponding α-amino esters by reducing agents such as NaBH₃CN. α-(N-Trimethylsilyl)imino esters were treated with methanol to afford 2-alkoxycarbonylimidazole-4(2H)-ones via dimerization of the intermediate α-imino esters.