Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

Sebastian C. Cosgrove, Shahed Hussain, Nicholas J. Turner, Stephen P. Marsden

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)-catalyzed addition/condensation sequence of alkyl vinyl ketones and aminophenylboronic acids. The resulting tetrahydroquinolines were thereafter shown to be substrates for the flavin-dependent enzyme cyclohexylamine oxidase, and preparative-scale deracemizations have been demonstrated on these high-value targets.

    Original languageEnglish
    Pages (from-to)5570-5573
    Number of pages4
    JournalACS Catalysis
    Volume8
    Issue number6
    Early online date14 May 2018
    DOIs
    Publication statusPublished - 1 Jun 2018

    Keywords

    • alkaloidal tetrahydroquinoline
    • amine oxidase
    • biocatalysis
    • enzymatic deracemization
    • rhodium catalysis

    Research Beacons, Institutes and Platforms

    • Manchester Institute of Biotechnology

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