The origin of chemical and configurational stability of chiral nonracemic tert-butyl aziridinecarboxylate anions

The origin of good chemical and configurational stability of aziridine este r anions derived from (R)-(-) -phenylglycinol has been investigated. Kineti c acidity seems to play an important role in the deprotonation step and che mical stability of the anionic species. Spectroscopic investigations showed that the good overall retention of configuration was governed by the direc ting effect of the nitrogen atom, which acts as a stereogenic centre in the alkylation step of the enolate intermediate.