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

Abstract

Herein we present a highly efficient, light-mediated, deoxygenative protocol to access γ-oxo-α-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 γ-oxo-α-amino acids bearing a wide range of functional groups (e.g., Cl, CN, furan, thiophene, Bpin) in synthetically useful yields (∼60% average yield). To further highlight the utility of the methodology, several deprotection and derivatization reactions were carried out.