T. Katagiri et al., General syntheses of optically active alpha-trifluoromethylated amines viaring-opening reactions of N-benzyl-2-trifluoromethylaziridine, J ORG CHEM, 64(20), 1999, pp. 7323-7329
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.