Conversion of Aziridinemethanol Sulfonate Esters to Allylic Amines via Tellurium Chemistry1

Sulfonate esters of aziridinemethanols are converted to allylic amines by treatment with telluride ion obtained by reduction of elemental tellurium. In the course of the reaction, tellurium(0) is reformed and may be reused, thus removing the need to dispose of a key reagent. The telluride reaction yields optically active allylic amines from optically active aziridinemethanols. In contrast to many ring-openings of aziridines by nucleophiles, activation by an electron-withdrawing substituent on nitrogen is not necessary and is even detrimental.