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Enantioselective Synthesis of (R)-2-Arylpropanenitriles Catalysed by Ene-Reductases in Aqueous Media and in Biphasic Ionic Liquid–Water Systems

Authors

  • Prof. Elisabetta Brenna,

    Corresponding author
    1. Department of Chemistry, Materials and Chemical Engineering, “Giulio Natta” Politecnico di Milano, Piazza Leonardo Da Vinci 32, 20133 Milano (Italy), Fax: (+39) 02-23993180
    • Department of Chemistry, Materials and Chemical Engineering, “Giulio Natta” Politecnico di Milano, Piazza Leonardo Da Vinci 32, 20133 Milano (Italy), Fax: (+39) 02-23993180

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  • Michele Crotti,

    1. Department of Chemistry, Materials and Chemical Engineering, “Giulio Natta” Politecnico di Milano, Piazza Leonardo Da Vinci 32, 20133 Milano (Italy), Fax: (+39) 02-23993180
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  • Dr. Francesco G. Gatti,

    1. Department of Chemistry, Materials and Chemical Engineering, “Giulio Natta” Politecnico di Milano, Piazza Leonardo Da Vinci 32, 20133 Milano (Italy), Fax: (+39) 02-23993180
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  • Alessia Manfredi,

    1. Department of Chemistry, Materials and Chemical Engineering, “Giulio Natta” Politecnico di Milano, Piazza Leonardo Da Vinci 32, 20133 Milano (Italy), Fax: (+39) 02-23993180
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  • Dr. Daniela Monti,

    1. Istituto di Chimica del Riconoscimento Molecolare, C.N.R. Via Mario Bianco 9, 20131 Milano (Italy)
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  • Dr. Fabio Parmeggiani,

    Corresponding author
    1. Department of Chemistry, Materials and Chemical Engineering, “Giulio Natta” Politecnico di Milano, Piazza Leonardo Da Vinci 32, 20133 Milano (Italy), Fax: (+39) 02-23993180
    • Department of Chemistry, Materials and Chemical Engineering, “Giulio Natta” Politecnico di Milano, Piazza Leonardo Da Vinci 32, 20133 Milano (Italy), Fax: (+39) 02-23993180

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  • Sara Santangelo,

    1. Department of Chemistry, Materials and Chemical Engineering, “Giulio Natta” Politecnico di Milano, Piazza Leonardo Da Vinci 32, 20133 Milano (Italy), Fax: (+39) 02-23993180
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  • Dr. Davila Zampieri

    1. Department of Chemistry, Materials and Chemical Engineering, “Giulio Natta” Politecnico di Milano, Piazza Leonardo Da Vinci 32, 20133 Milano (Italy), Fax: (+39) 02-23993180
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Abstract

The enantioselective reduction of α-methylene nitrile derivatives catalysed by ene-reductases affords the corresponding (R)-2-arylpropanenitriles with high conversion values. The reaction is investigated either in aqueous medium (with an organic cosolvent or by loading the substrate onto hydrophobic resins) or in a biphasic ionic liquid–water system. The use of ionic liquids, herein with isolated ene-reductases, is found to improve the work-up and the substrate recovery method. The synthetic manipulation of the final chiral nitrile derivatives indicates how this biocatalysed method can be exploited for the preparation of a wide range of chiral compounds.

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