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Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis.

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.

SUBMITTER: Faraggi TM

PROVIDER: S-EPMC9162430 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis.

Faraggi Tomer M TM Rouget-Virbel Caroline C Rincón Juan A JA Barberis Mario M Mateos Carlos C García-Cerrada Susana S Agejas Javier J de Frutos Oscar O MacMillan David W C DWC

Organic process research & development 20210726 8

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 technol ...[more]

PMID: 35663840

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