A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling.
Shengyang NiAlberto F Garrido-CastroRohan R MerchantJustine N de GruyterDaniel C SchmittJames J MousseauGary M GallegoShouliang YangMichael R CollinsJennifer X QiaoKap-Sun YeungDavid R LangleyMichael A PossPaul M ScolaTian QinPhil S BaranPublished in: Angewandte Chemie (International ed. in English) (2018)
The direct union of primary, secondary, and tertiary carboxylic acids with a chiral glyoxylate-derived sulfinimine provides rapid access into a variety of enantiomerically pure α-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic α-amino acids, including both unprecedented structures and those of established industrial value. The described method performs well in high-throughput library synthesis, and has already been implemented in three distinct medicinal chemistry campaigns.