Intramolecular Benzoin Reaction Catalyzed by Benzaldehyde Lyase from Pseudomonas Fluorescens Biovar I

Karel Hernández, Teodor Parella, Giovanna Petrillo, Isabel Usón, Claudia M. Wandtke, Jesús Joglar, Jordi Bujons, Pere Clapés

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    10 Citations (Scopus)

    Abstract

    © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Intramolecular benzoin reactions catalyzed by benzaldehyde lyase from Pseudomonas fluorescens biovar I (BAL) are reported. The structure of the substrates envisaged for this reaction consists of two benzaldehyde derivatives linked by an alkyl chain. The structural requirements needed to achieve the intramolecular carbon–carbon bond reaction catalyzed by BAL were established. Thus, a linker consisting of a linear alkyl chain of three carbon atoms connected through ether-type bonds to the 2 and 2′ positions of two benzaldehyde moieties, which could be substituted with either Cl, Br, or OCH3 at either the 3 and 3′ or 5 and 5′ positions, were suitable substrates for BAL. Reactions with 61–84 % yields of the intramolecular product and ee values between 64 and 98 %, were achieved.
    Original languageEnglish
    Pages (from-to)5304-5307
    JournalAngewandte Chemie - International Edition
    Volume56
    Issue number19
    DOIs
    Publication statusPublished - 1 Jan 2017

    Keywords

    • asymmetric catalysis
    • biocatalysis
    • C−C coupling
    • enzymes
    • macrocycles

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