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, SpainRead the publication that featured this abstract
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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