The direct chiral Lewis acidic enantioselective chlorination and fluorination of β-keto phosphonates is presented; the chlorination proceeds in high yields and with up to 94% ee using NCS as the chloro source, while the fluorination with (PhSO₂)₂NF (NFSI) gives the optically active α-fluoro-β-keto phosphonates in moderate to good yields and with up to 91% ee.