Access to Deuterated Unnatural α-Amino Acids and Peptides by Photochemical Acyl Radical Addition
Li Liu, Zikun Deng, Kun Xu, Pengxing Jiang, Hongguang Du, Jiajing Tan
Abstract
A visible-light-enabled, photocatalyst-free conjugate addition reaction of dehydroamino acids is disclosed. Employing 4-acyl-1,4-dihydropyridines as both a radical reservoir and reductant, various β-acyl α-amino acids and their deuterated analogues were obtained in good results. Both late-stage peptide modification and stereoselective synthesis of chiral oxazolidinones are successfully achieved. The protocol is characterized by mild conditions and efficient derivatization, thus unlocking a novel blueprint to access unnatural amino acid derivatives, important building blocks with potential application in the peptidomimetic toolbox.
Topics & Concepts
ChemistryPeptidomimeticAmino acidConjugateDerivatizationStereoselectivityCombinatorial chemistryPeptideOrganic chemistryCatalysisBiochemistryHigh-performance liquid chromatographyMathematicsMathematical analysisChemical Reactions and IsotopesRadical Photochemical ReactionsChemical Synthesis and Analysis