Preparation of Optically Pure α-Trifluoromethyl-α-amino Acids from N-Tosyl-2-trifluoromethyl-2-alkyloxycarbonyl Aziridine

The preparation of optically pure alpha-trifluoromethyl-alpha-amino acids from N-tosyl-2-trifluoromethyl-2-alkyloxycarbonylaziridine is described. Optically pure aziridine was prepared with a 60% yield via three steps from optically pure 2,3-epoxy-1,1,1-trifluoropropane (TFPO). Ring-opening reactions of the aziridine with a variety of nucleophiles and subsequent deprotection of the N-tosyl moieties gave the optically pure beta-substituted-alpha-trifluoromethyl-alpha-amino acids in moderate to good yields (up to 85%) without racemization at the quaternary stereogenic center of the amino acid.