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Enantioselective aziridination of alkenes with N-aminophthalimide in the presence of lead tetraacetate-mediated chiral ligand.

Organic letters (2002-04-02)
Kung-Shou Yang, Kwunmin Chen
RESUMEN

[reaction: see text] Reaction of various N-enoyl oxazolidinones 5a-f with N-aminophthalimide and lead tetraacetate in the presence of camphor-derived chiral ligands provides the desired N-phthalimidoaziridines 6a-f in good to high enantiomeric excess (67-95% ee) at 0 degrees C within 15 min. The absolute stereochemistry of the corresponding aziridine derivatives was established by chemical correlations.

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Sigma-Aldrich
N-Aminophthalimide, technical grade, 90%