The first catalytic enantioselective hydroxylation reaction of both 3-aryl and 3-alkyl-2- oxindoles using the DBFOX-Zn (II) complex, leading to pharmaceutically important chiral 3- hydroxy-2-oxindoles was described. The structure of oxidant was found to play an important role to increase the enantioselectivity. The methodology has successfully applied to the highly enantioselective hydroxylation of β-keto esters using the DBFOX-Ni (II) complex.