General syntheses of optically active alpha-trifluoromethylated amines viaring-opening reactions of N-benzyl-2-trifluoromethylaziridine

Syntheses of optically active trifluoromethylated amines via ring-opening r eactions of optically active N-benzyl-2-trifluoromethylaziridine were achie ved. Proton-catalyzed ring-opening reactions of the 2-trifluoromethylazirid ine proceeded very smoothly, while the compound was found to be inert towar d nucleophiles; thus, the trifluoromethylaziridine itself cannot be ring-op ened by nitrogen or carbon nucleophiles. The N-alkylated aziridinium ion of trifiuoromethylaziridine was highly reactive to undergo smooth ring-openin g by nitrogen and carbon nucleophiles.