Parallel kinetic resolution of aziridines <i>via</i> chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening
Juan Liu, Yi-Ying Du, Yu‐Shi He, Yan Liang, Shangzhong Liu, Yiyi Li, Yiming Cao
Abstract
We report a chiral phosphoric acid catalyzed apparent hydrolytic ring-opening reaction of racemic aziridines in a regiodivergent parallel kinetic resolution manner. Harnessing the acyloxy-assisted strategy, the highly stereocontrolled nucleophilic ring-opening of aziridines with water is achieved. Different kinds of aziridines are applicable in the process, giving a variety of enantioenriched aromatic or aliphatic amino alcohols with up to 99% yields and up to >99.5 : 0.5 enantiomeric ratio. Preliminary mechanistic study as well as product elaborations were inducted as well.
Topics & Concepts
Kinetic resolutionPhosphoric acidHydrolysisRing (chemistry)ChemistryCatalysisResolution (logic)Optically activeAmino acidCombinatorial chemistryStereochemistryOrganic chemistryEnantioselective synthesisBiochemistryComputer scienceArtificial intelligenceSynthesis and Catalytic ReactionsAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and Catalysis