Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis
Tomer M. Faraggi, Caroline Rouget-Virbel, Juan A. Rincón, Mario Barberis, Carlos Mateos, Susana Garcı́a-Cerrada, Javier Agejas, Óscar de Frutos, David W. C. MacMillan
Abstract
We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.
Topics & Concepts
Enantiopure drugElectrophileCombinatorial chemistryChemistryArylAmino acidCatalysisOrganic chemistryEnantioselective synthesisAlkylBiochemistryRadical Photochemical ReactionsChemical Synthesis and AnalysisSulfur-Based Synthesis Techniques