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Highly Enantioselective Reduction of α-Methylated Nitroalkenes

Authors

  • Dr. Edyta Burda,

    1. Department of Chemistry and Pharmacy, University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
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  • Tina Reß,

    1. Department of Chemistry and Pharmacy, University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
    2. Present address: Faculty of Chemistry, Bielefeld University, Universitätsstrasse 25, 33615 Bielefeld (Germany)
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  • Till Winkler,

    1. Institute for Molecular Enzyme Technology at the Heinrich-Heine-University of Düsseldorf, Research Centre Jülich, Stetternicher Forst, 52426 Jülich (Germany)
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  • Carolin Giese,

    1. Department of Chemistry and Pharmacy, University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
    2. Present address: Faculty of Chemistry, Bielefeld University, Universitätsstrasse 25, 33615 Bielefeld (Germany)
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  • Xenia Kostrov,

    1. Department of Chemistry and Pharmacy, University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
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  • Tobias Huber,

    1. Department of Chemistry and Pharmacy, University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
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  • Prof. Dr. Werner Hummel,

    Corresponding author
    1. Institute for Molecular Enzyme Technology at the Heinrich-Heine-University of Düsseldorf, Research Centre Jülich, Stetternicher Forst, 52426 Jülich (Germany)
    • Werner Hummel, Institute for Molecular Enzyme Technology at the Heinrich-Heine-University of Düsseldorf, Research Centre Jülich, Stetternicher Forst, 52426 Jülich (Germany)

      Harald Gröger, Department of Chemistry and Pharmacy, University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)

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  • Prof. Dr. Harald Gröger

    Corresponding author
    1. Department of Chemistry and Pharmacy, University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)
    2. Present address: Faculty of Chemistry, Bielefeld University, Universitätsstrasse 25, 33615 Bielefeld (Germany)
    • Werner Hummel, Institute for Molecular Enzyme Technology at the Heinrich-Heine-University of Düsseldorf, Research Centre Jülich, Stetternicher Forst, 52426 Jülich (Germany)

      Harald Gröger, Department of Chemistry and Pharmacy, University of Erlangen-Nürnberg, Henkestrasse 42, 91054 Erlangen (Germany)

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  • We thank the state of North Rhine-Westphalia for generous financial support within the supporting program “Transfer NRW: Science-to-Business PreSeed”.

Abstract

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Highly selective: The reduction of α-methyl-substituted nitroalkenes succeeds in a highly enantioselective fashion with an ene reductase from Gluconobacter oxydans. Under optimized reaction conditions the desired nitroalkanes are formed with enantiomeric excesses of up to 95% in these biotransformations.

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