Visible Light-Promoted Deracemization of α-Amino Aldehyde by Synergistic Chiral Primary Amine and Hypervalent Iodine Catalysis

α-Amino aldehydes, as versatile chiral synthons, are easily racemized under normal acid or base conditions, seriously limiting their synthetic potentials. We report herein an effective deracemization of α-amino aldehydes by a synergistic chiral primary amine and hypervalent iodine catalysis under visible light. The developed catalytic system allows for the on-demand production of α-Boc- or Cbz-protected amino aldehydes with high enantioselectivity. Mechanistic studies verified a photochemical <i>Z</i>-<i>E</i> isomerization mechanism that drives the deracemization process.