4.7 Article

Integrated Flow Synthesis of α-Amino Acids by In Situ Generation of Aldimines and Subsequent Electrochemical Carboxylation

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 22, Pages 15953-15960

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00821

Keywords

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Funding

  1. CREST (JST) [JPMJCR18R1]
  2. JSPS, Japan [20H02513, 20K21106]
  3. Grants-in-Aid for Scientific Research [20K21106, 20H02513] Funding Source: KAKEN

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The synthesis of alpha-amino acids was efficiently carried out in a continuous flow system without the need for stoichiometric amounts of metal reagents or highly toxic cyanide reagents, producing high to moderate yields.
The synthesis of alpha-amino acids was carried out in a continuous flow system. In this system, aldimines were efficiently generated in situ via the dehydration-condensation of aldehydes with anilines in a desiccant bed column filled with 4 angstrom molecular sieves desiccant, followed by reaction with CO2 in an electrochemical flow microreactor to afford the alpha-amino acids in high to moderate yields. The present system can provide alpha-amino acids without using stoichiometric amounts of metal reagents or highly toxic cyanide reagents.

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