Preparation of optically pure α-trifluoromethyl-α-amino acids from N-tosyl-2-trifluoromethyl-2-alkyloxycarbonyl aziridine.

The preparation of optically pure α-trifluoromethyl-α-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 β-substituted-α-trifluoromethyl-α-amino acids in moderate to good yields (up to 85%) without racemization at the quaternary stereogenic center of the amino acid.

Alpha-trifluoromethylated carbanion synthons.

Trifluomethylated organic compounds often have properties that make them suitable for diverse applications, including materials science, agrochemistry, and pharmaceutical industry. But of all the therapeutic drugs currently available, about 10% of them have a partially fluorinated moiety. Thus, a great deal of attention is being paid to the development of reliable methodologies for trifluoromethylation.

Palladium-catalyzed chloroimination of imidoyl chlorides to a triple bond: an intramolecular reaction leading to 4-chloroquinolines.

In this paper, a new type of effective chloroimination was reported. This reaction afforded 4-chloro-2-perfluoroalkyl quinolines from fluorinated imidoyl chlorides in high yields. This is the first achievement of oxidative addition-reductive elimination type C-Cl bond activation by chloropalladation.