4.7 Article

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

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 13, Pages 2744-2754

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000238

Keywords

Asymmetric catalysis; chiral 3-amino oxindoles; aza Friedel-Crafts reaction; bifunctional thioureas; flow chemistry; supported catalysts

Funding

  1. Junta de Castilla y Leon [FEDER-VA115P17, VA149G18]

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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.

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