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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

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

Shatskiy Andrey A Axelsson Anton A Stepanova Elena V EV Liu Jian-Quan JQ Temerdashev Azamat Z AZ Kore Bhushan P BP Blomkvist Björn B Gardner James M JM Dinér Peter P Kärkäs Markus D MD

Chemical science 20210303 15

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived <i>N</i>-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 amoun ...[more]

PMID: 34168785

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