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A Simple Enantioconvergent and Chemoenzymatic Synthesis of Optically Active α-Substituted Amides

Authors

  • Dr. Wiktor Szymański,

    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
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  • Alja Westerbeek,

    1. Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
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  • Prof. Dr. Dick B. Janssen,

    Corresponding author
    1. Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
    • Department of Biochemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
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  • Prof. Dr. Ben L. Feringa

    Corresponding author
    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
    • Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
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  • We thank Theodora Tiemersma-Wegman and Monique Smith for their technical assistance with HPLC and GC analyses.

Abstract

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Simple and efficient: The combination of an enzymatic, enantioinverting reaction with simple follow-up processes allows the transformation of readily available racemic compounds into versatile chiral α-substituted amides (see picture; Ms=methanesulfonyl). These important building blocks are prepared in high overall yield and enantiomeric excess; the elimination of intermediate purification steps results in a time- and cost-efficient process.

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