Supported Bifunctional Chiral Thioureas as Catalysts in the Synthesis of 3‐Amino‐2‐Oxindoles through Enantioselective aza‐Friedel‐Crafts Reaction: Application in Continuous Flow Processes
Marta Rodríguez‐Rodríguez, Alicia Maestro, José M. Andrés, Rafaël Pedrosa
Abstract
Abstract Supported cinchone‐derived thioureas promote highly enantioselective aza‐Friedel‐Crafts reaction of different naphthols with a variety of N‐Boc ketimines derived from isatin. The catalysts are recoverable and reusable, and one of the supported catalysts has been used in a flow process allowing the synthesis of 3‐amino‐2‐oxindole derivatives in multigram scale with high yield and enantioselectivity. magnified image
Topics & Concepts
ChemistryEnantioselective synthesisBifunctionalFriedel–Crafts reactionOxindoleCatalysisIsatinYield (engineering)Organic chemistryThioureaOrganocatalysisCombinatorial chemistryMaterials scienceMetallurgyInnovative Microfluidic and Catalytic Techniques InnovationOxidative Organic Chemistry ReactionsChemical Synthesis and Analysis