Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

• Tomer M. Faraggi^a
• Caroline Rouget-Virbel^a
• Juan A. Rincón^b
• Mario Barberis^b
• Carlos Mateos^b
• Susana García-Cerrada^b
• Javier Agejas^b
• Oscar de Frutos^b
• David W. C. MacMillan^a

• ^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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