CONVERSION OF AZIRIDINEMETHANOL SULFONATE ESTERS TO ALLYLIC AMINES VIA TELLURIUM CHEMISTRY

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