An Organocatalytic Kinetic Resolution of Aziridines by Thiol Nucleophiles
Song Sun, Zhaobin Wang, Shijia Li, Cong Zhou, Lijuan Song, Hai Huang, Jianwei Sun
Abstract
We report the first organocatalytic kinetic resolution of unactivated aziridines by sulfur nucleophiles with excellent enantioselectivity. A suitable chiral phosphoric acid was found to catalyze the intermolecular ring opening under mild conditions, furnishing a range of highly enantioenriched β-amino thioethers and aziridines, both of which are useful synthetic building blocks.
Topics & Concepts
NucleophileChemistryKinetic resolutionIntermolecular forcePhosphoric acidThiolOrganocatalysisSulfurRing (chemistry)Combinatorial chemistryResolution (logic)Organic chemistryCatalysisMoleculeEnantioselective synthesisComputer scienceArtificial intelligenceSynthesis and Catalytic ReactionsAsymmetric Synthesis and CatalysisSulfur-Based Synthesis Techniques