A convenient synthesis of aziridine-2-carboxylic esters
作者:Johan Legters、Lambertus Thijs、Binne Zwanenburg
DOI:10.1002/recl.19921110101
日期:——
Optically active oxirane-2-carboxylic esters, prepared from allylic alcohols employing the Sharpless epoxidation, were treated with sodium azide. The azido alcohols obtained were subsequently converted into aziridine-2-carboxylicesters by reaction with triphenylphosphine, in good yields and with high optical purity. Various racemic oxirane-2-carboxylic esters were subjected to the same sequence of
Isomerization of glycidic esters and nitriles to the corresponding 2-hydroxy-3-alkenoates and their nitrile derivatives occurred on treatment with triphenylsilyl perchlorate or electrogenerated acid (EG acid). The cyanohydrin moiety of the nitriles 4 was transformed to a formyl group, giving the corresponding enals on treatment with weak base.