Stereoselective synthesis of unnatural α-amino acid derivatives through photoredox catalysis.

ABSTRACT: A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived N-sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. Alternative mechanisms for the developed transformation are discussed and corroborated by experimental and computational studies.

SUBMITTER: Shatskiy A 

PROVIDER: S-EPMC8179686 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature