A facile and highly diastereoselective aziridination of chiral camphor n-enoylpyrazolidinones with n-aminophthalimide.
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.
Department of Chemistry, National Taiwan Normal University, 88 Sec. 4 TingChow Road, Taipei, Taiwan 116, ROC.
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Yang
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Chen