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

Autor:	Elena V. Stepanova, Björn Blomkvist, Bhushan P. Kore, A. Z. Temerdashev, Peter Dinér, Jian-Quan Liu, Anton Axelsson, James M. Gardner, Andrey Shatskiy, Markus D. Kärkäs
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Chemistry Imine Photoredox catalysis General Chemistry Combinatorial chemistry Catalysis Amino acid chemistry.chemical_compound Photocatalysis Stereoselectivity Acid radical Derivatization
Zdroj:	Chemical Science
ISSN:	2041-6539 2041-6520
Popis:	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. 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4e71f141149d2279c87cff95c4beac34 https://doi.org/10.1039/d1sc00658d Zobrazit plný text záznamu