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

Shengyang Ni, Alberto F. Garrido-Castro, Rohan R. Merchant, Justine N. de Gruyter, Daniel C. Schmitt, James J. Mousseau, Gary M. Gallego, Shouliang Yang, Michael R. Collins, Jennifer X. Qiao, Kap Sun Yeung, David R. Langley, Michael A. Poss, Paul M. Scola, Tian Qin, Phil S. Baran

Research output: Contribution to journalArticle

29 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)14560-14565
Number of pages6
JournalAngewandte Chemie - International Edition
Volume57
Issue number44
DOIs
StatePublished - Oct 26 2018
Externally publishedYes

Keywords

  • amino acid synthesis
  • decarboxylative radical addition
  • library synthesis
  • redox-active esters
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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    Ni, S., Garrido-Castro, A. F., Merchant, R. R., de Gruyter, J. N., Schmitt, D. C., Mousseau, J. J., Gallego, G. M., Yang, S., Collins, M. R., Qiao, J. X., Yeung, K. S., Langley, D. R., Poss, M. A., Scola, P. M., Qin, T., & Baran, P. S. (2018). A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling. Angewandte Chemie - International Edition, 57(44), 14560-14565. https://doi.org/10.1002/anie.201809310