A General Amino Acid Synthesis Enabled by Innate Radical Cross‐Coupling. (15th October 2018)

• Record Type: Journal Article
• Authors: Ni, Shengyang; Garrido‐Castro, Alberto F.; Merchant, Rohan R.; de Gruyter, Justine N.; Schmitt, Daniel C.; Mousseau, James J.; Gallego, Gary M.; Yang, Shouliang; Collins, Michael R.; Qiao, Jennifer X.; Yeung, Kap‐Sun; Langley, David R.; Poss, Michael A.; Scola, Paul M.; Qin, Tian; Baran, Phil S.
• Is Part Of: Angewandte Chemie. Volume 130:Number 44(2018)
• Page Start: 14768
• Page End: 14773
• Publication Date: 2018-10-15
• Subjects: Aminosäuresynthese -- Bibliotheksynthese -- Decarboxylierende radikalische Addition -- Redoxaktive Ester -- Synthesemethoden; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201809310
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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.