Synthesis of Enantioenriched α-Deuterated α-Amino Acids Enabled by an Organophotocatalytic Radical Approach

• DOI: 10.1021/acs.orglett.0c00154
• Publication Date: 2020-02-11T20:43:41Z
• Authors: Peng Ji; Yueteng Zhang; Yue Dong; He Huang; Yongyi Wei; Wei Wang
• Keywords: Free Radicals; Molecular Structure; Carboxylic Acids; Stereoisomerism; Amino Acids; Photochemical Processes; Oxidation-Reduction; 01 natural sciences; Catalysis; Oxazolidinones; 0104 chemical sciences

A mild, versatile organophotoredox protocol has been developed for the preparation of diverse, enantioenriched α-deuterated α-amino acids. Distinct from well-established two-electron transformations, this radical-based strategy offers unrivaled capacity convergent unification readily accessible feedstock carboxylic acids and a chiral methyleneoxazolidinone fragment simultaneous highly diastereo-, chemo-, regioselective incorporation deuterium. Furthermore, approach addressed long-standing challenge installation sterically demanding side chains into