Synthesis of S-trifluoromethyl-containing α-amino acids from sodium trifluoromethanesulfinate and dithio-amino acids

Article abstract of DOI:10.1016/0022-1139(93)02982-K

N-Protonated or N-acetylated dimethyl cystinates and homocystinates react with sodium trifluoromethanesulfinate and t-butyl hydroperoxide to yield the corresponding derivatives of methyl S-trifluoromethyl cysteinate and homocysteinate in a stereospecific manner.Methyl S-trifluoromethyl-N-acetyl cysteinate and homocysteinate are readily saponified, without racemization, by sodium hydrogen carbonate in a water/methanol mixture.