A Facile and Highly Diastereoselective Aziridination of Chiral Camphor <i>N</i>-Enoylpyrazolidinones with <i>N</i>-Aminophthalimide

Abstract

Reaction of various chiral camphor N-enoylpyrazolidinones 2a-g with N-aminophthalimide in the presence of lead tetraacetate in CH(2)Cl(2) proceed smoothly afford the corresponding N-phthalimidoaziridines (3a-e, 4f-g) with excellent material yields (86-95%) at room temperature in 5 min. High levels of diastereoselectivities (up to >95:5 dr) were obtained. The solvent effect was investigated, and the auxiliary can be easily recovered in high yields under mild reaction conditions.