Enantioselective Construction of Vicinal Quaternary-Tetrasubstituted Carbon Stereocenters by Copper-Catalyzed Decarboxylative Propargylic Substitution
Yong You, Tingting Li, Ting-Jia Sun, Yanping Zhang, Zhen‐Hua Wang, Jian‐Qiang Zhao, Wei‐Cheng Yuan
Abstract
Enantioselective construction of vicinal tetrasubstituted carbon stereocenters is a formidable challenge in organic synthesis. A copper-catalyzed asymmetric decarboxylative propargylic substitution with 3-amino oxindoles as trisubstituted carbon nucleophiles and propargylic cyclic carbonates as tertiary carbon electrophiles was developed. A range of 3-amino-3,3'-disubstituted oxindoles bearing vicinal quaternary-tetrasubstituted carbon stereocenters were obtained in high yields and good to excellent stereoselectivities (up to 98% yield, >20:1 dr, and 98.5:1.5 er).
Topics & Concepts
StereocenterChemistryEnantioselective synthesisVicinalSubstitution (logic)CopperCatalysisQuaternary carbonCarbon fibersOrganic chemistryStereochemistryCombinatorial chemistryMathematicsAlgorithmComposite numberComputer scienceProgramming languageAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsAsymmetric Hydrogenation and Catalysis