Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

    • Tomer M. Faraggia
    • Caroline Rouget-Virbela
    • Juan A. Rincónb
    • Mario Barberisb
    • Carlos Mateosb
    • Susana García-Cerradab
    • Javier Agejasb
    • Oscar de Frutosb
    • David W. C. MacMillana
    • aMerck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States
    • bCentro de Investigación Eli Lilly, S. A. Avda de la Industria 30, Alcobendas-Madrid 28108, Spain

    We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.

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