The synthesis, characterisation and single crystal X-ray structures of square planar Ni(II) chiral Schiff base complexes with N2O2-type Ligands have been described. These catalysts were used for enantioselective epoxidation of non-functionalised alkenes viz. 1-hexene, 1-octene, styrene, 4-chloro-, 4-nitrostyrene and 1,2-dihydronaphthalene using NaOCl as oxidant, giving excellent conversions with long chain alkenes while ee's were moderate to good. A mechanism for the Ni(II)-catalysed epoxidation with NaOCl is proposed.