GENERAL SYNTHESES OF OPTICALLY ACTIVE ALPHA -TRIFLUOROMETHYLATED AMINES VIA RING-OPENING REACTIONS OF N-BENZYL-2-TRIFLUOROMETHYLAZIRIDINE

Syntheses of optically active trifluoromethylated amines via ring-opening reactions of optically active N-benzyl-2-trifluoromethylaziridine were achieved. Proton-catalyzed ring-opening reactions of the 2-trifluoromethylaziridine proceeded very smoothly, while the compound was found to be inert toward nucleophiles; thus, the trifluoromethylaziridine itself cannot be ring-opened by nitrogen or carbon nucleophiles. The N-alkylated aziridinium ion of trifluoromethylaziridine was highly reactive to undergo smooth ring-opening by nitrogen and carbon nucleophiles.