Synthesis of Unnatural Amino Acids via Ni/Ag Electrocatalytic Cross-Coupling
Gabriele Laudadio, Philipp Neigenfind, Rajesh Chebolu, Vanna D. Blasczak, Shambabu Joseph Maddirala, Maximilian D. Palkowitz, Philippe N. Bolduc, Michael C. Nicastri, Ravi Kumar Puthukanoori, Bheema Rao Paraselli, Phil S. Baran
Abstract
A simple protocol is outlined herein for rapid access to enantiopure unnatural amino acids (UAAs) from trivial glutamate and aspartate precursors. The method relies on Ag/Ni-electrocatalytic decarboxylative coupling and can be rapidly conducted in parallel (24 reactions at a time) to ascertain coupling viability followed by scale-up for the generation of useful quantities of UAAs for exploratory studies.
Topics & Concepts
Enantiopure drugChemistryAmino acidCoupling (piping)Combinatorial chemistryComputational chemistryOrganic chemistryBiochemistryEnantioselective synthesisCatalysisMechanical engineeringEngineeringChemical Synthesis and AnalysisRadical Photochemical ReactionsSulfur-Based Synthesis Techniques