Reversal of regioselection in the asymmetric aminohydroxylation of cinnamates

Article abstract of DOI:10.1016/S0040-4039(98)00350-5

Use of cinchona ligands with an anthraquinone (AQN) core, in place of the usual phthalazine (PHAL) core, in the asymmetric aminohydroxylation of cinnamates causes dramatic reversal of the regioselection, so that phenyl serines are obtained in high enantiomeric excess. Hence, the regioselectivity outcome (i.e. isoserine vs. serine) is controlled by the ligand and not the substrate.