Abstract The carbonyl epoxide rearrangement can be extended to δ, ε-epoxy imines. The reaction takes place by intramolecular nucleophilic displacement involving attack of the imino nitrogen on the epoxide ring. A high degree of stereospecificity is observed in this process which provides a facile route to 6-oxa-8-azabicyclo [3.2. 1] octanes.
