Diastereoselective synthesis of 3'-unsubstituted N-BOC- Aziridine from a readily available chiral α-β-unsaturated imide

Article abstract of DOI:10.1016/S0040-4020(98)00459-1

The conjugate addition of N-BOC-O-benzoyl hydroxylamine catalysed by sodium hydride to a chiral α,β-unsaturated imide gives a 3'-(BOC benzoyloxyaminopropanoyl) derivative. This undergoes cyclization upon treatment with sodium or lithium bases to give a 3'-unsubstituted N-BOC aziridine-2-imide in good yield and diastereoselectivity. When N-BOC-O-benzoyl hydroxylamine is deprotonated with stoichiometric lithium or sodium bases, the intermediate enolate resulting from the 1,4-addition spontaneously undergoes cyclization affording in a single step the N-BOC aziridine in higher yield.