Remotely Controlled Iridium-Catalyzed Asymmetric Hydrogenation of Terminal 1,1-Diaryl Alkenes

Authors

  • Dr. Tatiana Besset,

    Corresponding author
    1. Supramolecular and Homogeneous Catalysis, van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam (The Netherlands) http://www.science.uva.nl/research/imc/HomKat
    2. Current address: Laboratory COBRA UMR 6014 & FR 3038, IRCOF, Université de Rouen, 1, Rue Tesnière, 76821 Mont St Aignan Cedex (France)
    • Supramolecular and Homogeneous Catalysis, van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam (The Netherlands) http://www.science.uva.nl/research/imc/HomKat===

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  • Dr. Rafael Gramage-Doria,

    1. Supramolecular and Homogeneous Catalysis, van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam (The Netherlands) http://www.science.uva.nl/research/imc/HomKat
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  • Prof. Dr. Joost N. H. Reek

    Corresponding author
    1. Supramolecular and Homogeneous Catalysis, van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam (The Netherlands) http://www.science.uva.nl/research/imc/HomKat
    • Supramolecular and Homogeneous Catalysis, van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam (The Netherlands) http://www.science.uva.nl/research/imc/HomKat===

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  • Eastman Chemical Company and the Rubicon Program of the NWO are acknowledged for financial support to T.B. and R.G.-D., respectively.

Abstract

original image

Working together: The presence of a remote directing group on terminal 1,1-diaryl and 1,1-dialkyl alkenes led to high and unprecedented enantioselectivity in iridium-catalyzed asymmetric hydrogenation (see scheme). This strategy offers efficient synthetic pathways towards valuable enantiomerically enriched 1,1-diaryl and 1,1-dialkyl alkanes. Moreover, the directing group can be further functionalized.

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