Synthesis of γ-Oxo-α-amino Acids via Radical Acylation with Carboxylic Acids

Herein we present a highly efficient, light-mediated, deoxygenative protocol to access gamma-oxo-alpha-amino acid derivatives. This radical methodology employs photoredox catalysis, in combination with triphenylphosphine, to generate acyl radicals from readily available (hetero)aromatic and vinylic carboxylic acids. This approach allows for the straightforward synthesis of gamma-oxo-alpha-amino acids bearing a wide range of functional groups (e.g., Cl, CN, furan, thiophene, Bpin) in synthetically useful yields (similar to 60% average yield). To further highlight the utility of the methodology, several deprotection and derivatization reactions were carried out.

Automated summary

This study presents a highly efficient light-mediated deoxygenative protocol for the synthesis of gamma-oxo-alpha-amino acid derivatives, achieving an average yield of around 60% with a variety of functional groups. The methodology's utility is further demonstrated through several deprotection and derivatization reactions.