Visible Light-Promoted Deracemization of α-Amino Aldehyde by Synergistic Chiral Primary Amine and Hypervalent Iodine Catalysis
Tianrun Pan, Xieyang Jiang, Mouxin Huang, Long Zhang, Sanzhong Luo
Abstract
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 Z – E isomerization mechanism that drives the deracemization process.
Topics & Concepts
ChemistryHypervalent moleculeIodineAldehydePrimary (astronomy)Amine gas treatingCatalysisCombinatorial chemistryOrganocatalysisOrganic chemistryEnantioselective synthesisAstronomyPhysicsOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsCatalytic C–H Functionalization Methods