Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

Tomer M. Faraggi, Caroline Rouget-Virbel, Juan A. Rincón, Mario Barberis, Carlos Mateos, Susana García-Cerrada, Javier Agejas, Oscar De Frutos, David W.C. Macmillan

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)1966-1973
Number of pages8
JournalOrganic Process Research and Development
Volume25
Issue number8
DOIs
StatePublished - Aug 20 2021

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • flow chemistry
  • heterocycles
  • nickel catalysis
  • photoredox catalysis
  • unnatural amino acids

Fingerprint

Dive into the research topics of 'Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis'. Together they form a unique fingerprint.

Cite this