26011-72-3Relevant academic research and scientific papers
A visible light-mediated, decarboxylative, desulfonylative Smiles rearrangement for general arylethylamine syntheses
Duong, Hung A.,Greaney, Michael F.,Whalley, David M.
supporting information, p. 11493 - 11496 (2020/10/12)
A decarboxylative, desulfonylative Smiles rearrangement is presented that employs activated-ester/energy transfer catalysis to decarboxylate β-amino acid derived starting materials at room-temperature under visible light irradiation. The radical Smiles rearrangement gives a range of biologically active arylethylamine products highly relevant to the pharmaceutical industry, chemical biology and materials science. The reaction is then applied to the synthesis of a chiral unnatural amino acid, 2-thienylalanine, used in the treatment of phenylketonuria. We also show how the reaction can proceed under metal-free and catalyst-free conditions.
