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A General Amino Acid Synthesis Enabled by Innate Radical Cross‐Coupling
Author(s) -
Ni Shengyang,
GarridoCastro 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 KapSun,
Langley David R.,
Poss Michael A.,
Scola Paul M.,
Qin Tian,
Baran Phil S.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201809310
Subject(s) - amino acid , modular design , chemistry , combinatorial chemistry , primary (astronomy) , simplicity , variety (cybernetics) , organic chemistry , computer science , biochemistry , physics , artificial intelligence , astronomy , operating system , quantum mechanics
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.