Abstract A preparatively simple diastereoselective synthesis of the amino acid chimera (1S, 3S)-1, 2, 3, 4-tetrahydroisoquinoline-1, 3-dicarboxylic acid from hexafluoroacetone- protected phenylalanine and glyoxylic acid hydrate via Pictet-Spengler reaction is described. The potential of the reaction of hexafluoroacetone-protected phenylalanine with other aldehydes was scrutinized.