The chiral 1R,5S-6-alkyl-6-aza-2R-menthoxy-3-oxa-4-oxobicyclo[3,1,0]hexane (5a～5d) containing two stereogenic centers were obtained in 41%～51% yields with e.e.≥98% via the tandem asymmetric Michael addition and internal nucleophilic substitution reaction of the chiron 3 with the primary amine 4 as a nucleophile. After the effective reduction of compounds 5 by LiAlH₄ in THF, the target molecules, meso-N-alkyl-2,3-bis(hydroxymethyl)aziridines (6a～6d) were obtained in 66%～91% yields. The chemical structures of 5 and 6 were readily confirmed by analytical and spectroscopic data. The proposed structures of optically active compounds were consistent with the stereochemistry and configuration of their molecules further confirmed by the X-ray crystallography of 5a and 6c. These results could provide a new synthetic route to the functionalized optically active aziridine derivatives.

Key words: tandem asymmetric reaction, aziridine derivative, optical activity, crystal structure