Anionic reactions of N-(trans-2,3-diphenylaziridin-1-yl)imines and their use as 1,1-dipoles in anionic cyclizations

Abstract

Reaction of N-(trans-2,3-diphenylaziridin-1-yl)imines with alkyllithiums and organocuprates afforded the desired addition products after consecutive fragmentations along with liberation of stilbene and nitrogen gas, while the reaction of N-(2-phenylaziridin-1-yl)imines under similar conditions gave an anomalous by-product. Anionic cyclizations of N(trans-2,3-diphenylaziridin-1-yl)imines using unactivated alkenes and alkynes as acceptors proceeded smoothly, yielding cyclized products in good yields.