Dynamic kinetic resolution of 2-phenylpropanal derivatives to yield β-chiral primary amines via bioamination

Christine S. Fuchs, Manuel Hollauf, Maximilian Meissner, Robert C. Simon, Tatiana Besset, Joost N.H. Reek, Waander Riethorst, Ferdinand Zepeck, Wolfgang Kroutil*

*Korrespondierende/r Autor/-in für diese Arbeit

    Publikation: Beitrag in einer FachzeitschriftArtikelBegutachtung

    Abstract

    The amination of racemic α-chiral aldehydes, 2-phenylpropanal derivatives, was investigated employing ω-transaminases. By medium and substrate engineering the optical purity of the resulting β-chiral chiral amine could be enhanced to reach optical purities up to 99% ee. Using enantiocomplementary ω-transaminases allowed us to access the (R)- as well as the (S)-enantiomer in most cases. It is important to note that the stereopreference of the ω-transaminases found for α-chiral aldehydes did not correlate with the stereopreference previously observed for the amination of methyl ketones. In one case the stereopreference switched even upon exchanging a methyl substituent to a methoxy group.

    Originalspracheenglisch
    Seiten (von - bis)2257-2265
    Seitenumfang9
    FachzeitschriftAdvanced Synthesis & Catalysis
    Jahrgang356
    Ausgabenummer10
    DOIs
    PublikationsstatusVeröffentlicht - 7 Juli 2014

    ASJC Scopus subject areas

    • Katalyse
    • Organische Chemie

    Fields of Expertise

    • Human- & Biotechnology

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