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

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journal contribution
posted on 01.06.2021, 15:35 by Kay Merkens, Francisco José Aguilar Troyano, Khadijah Anwar, Adrián Gómez-Suárez
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.