Synthesis of 3-Fluoro-3-aryl Oxindoles: Direct Enantioselective α Arylation of Amides

Authors

  • Linglin Wu,

    1. Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich (Switzerland)
    Search for more papers by this author
  • Laura Falivene,

    1. Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, 84084 Fisciano (Italy)
    Search for more papers by this author
  • Dr. Emma Drinkel,

    1. Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich (Switzerland)
    Search for more papers by this author
  • Sharday Grant,

    1. Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich (Switzerland)
    Search for more papers by this author
  • Priv.-Doz. Dr. Anthony Linden,

    1. Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich (Switzerland)
    Search for more papers by this author
  • Prof. Dr. Luigi Cavallo,

    1. Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, 84084 Fisciano (Italy)
    2. New address: King Abdullah University of Science and Technology (KAUST), Chemical and Life Sciences and Engineering, KAUST Catalysis Center, Thuwal 23955-6900 (Saudi Arabia)
    Search for more papers by this author
  • Prof. Dr. Reto Dorta

    Corresponding author
    1. Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich (Switzerland)
    2. New address: School of Chemistry and Biochemistry, University of Western Australia, 35 Stirling Highway, Crawley 6009 (Australia)
    • Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich (Switzerland)
    Search for more papers by this author

  • Support from the Swiss National Science Foundation (LW) is gratefully acknowledged.

Abstract

original image

Modus operandi: Catalytic access to the title compounds through a new asymmetric α-arylation protocol is reported (see scheme). These products are formed in good yields and excellent enantioselectivities by using a new and easily synthesized chiral N-heterocyclic carbene (NHC) ligand. Advanced DFT calculations reveal the properties of the NHC ligand and the mode of operation of the catalyst.

Ancillary