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

preprint
revised on 09.11.2020, 07:46 and posted on 10.11.2020, 09:55 by Kay Merkens, Francisco José Aguilar Troyano, Khadijah Anwar, Adrián Gómez Suárez
Herein we present a highly efficient, light-mediated, deoxygenative protocol to access g-oxo-a-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 g-oxo-aamino 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.

History

Email Address of Submitting Author

gomezsuarez@uni-wuppertal.de

Institution

Bergische Universität Wuppertal

Country

Germany

ORCID For Submitting Author

0000-0003-4822-6554

Declaration of Conflict of Interest

There is no conflict of interest

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