Catalytic aziridination of electron-deficient olefins with an N-chloro-N-sodio carbamate and application of this novel method to asymmetric synthesis

摘要

A new method for the aziridination of electron-deficient olefins using an N-chloro-N-sodio carbamate is described; the reaction was promoted by phase-transfer catalysis (solid-liquid) and afforded aziridines from α,β-unsaturated ketones, esters, sulfones and amides.rnAziridines, which are found in natural products, as well as in biologically active compounds, are important versatile building blocks in synthetic organic reactions. In particular, terminal aziridines are a potential source of two carbon atoms and one nitrogen atom, due to their facile ring-opening with various nucleophiles. Among the various methods available for the synthesis of aziridines, the aziridination of electron-deficient olefins, such as α,β-unsaturated carbonyl compounds, is useful because the products are readily converted into amino acid derivatives by ring-opening reactions.