Synthesis of N-methylene phosphonate aziridines: reaction scope and mechanistic insights

A series of N-carbamoyl aziridines has been treated by diethyl phosphite in the presence of n-BuLi to afford alpha-methylene phosphonate aziridines in modest yields. The study of the reaction's scopes and the analysis of byproducts indicated that this transformation proceeds via a unique mechanism. The mechanism that produces the alpha-methylene phosphonate relies on the use of BuLi, where both the lithium ion and then the presence of the nucleophilic butyl is essential. In addition, the nature of the final compound, either alpha-methylene phosphonate or alpha-methylene-gem-bisphosphonate derivatives containing an aziridine motif, is highly dependent on the nature of the base used.

Automated summary

N-carbamoyl aziridines were transformed into alpha-methylene phosphonate aziridines through a unique mechanism in the presence of n-BuLi and the nucleophilic butyl. The nature of the final compound depends on the base used.