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A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling.

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 ?-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic ?-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.

SUBMITTER: Ni S

PROVIDER: S-EPMC6352899 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling.

Ni Shengyang S Garrido-Castro Alberto F AF Merchant Rohan R RR de Gruyter Justine N JN Schmitt Daniel C DC Mousseau James J JJ Gallego Gary M GM Yang Shouliang S Collins Michael R MR Qiao Jennifer X JX Yeung Kap-Sun KS Langley David R DR Poss Michael A MA Scola Paul M PM Qin Tian T Baran Phil S PS

Angewandte Chemie (International ed. in English) 20181015 44

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 alread ...[more]

PMID: 30212610

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