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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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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]

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