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

J Org Chem. 2021 Nov 19;86(22):15953-15960. doi: 10.1021/acs.joc.1c00821. Epub 2021 Jun 21.

Abstract

The synthesis of α-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 Å molecular sieves desiccant, followed by reaction with CO2 in an electrochemical flow microreactor to afford the α-amino acids in high to moderate yields. The present system can provide α-amino acids without using stoichiometric amounts of metal reagents or highly toxic cyanide reagents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes*
  • Amino Acids*
  • Indicators and Reagents

Substances

  • Aldehydes
  • Amino Acids
  • Indicators and Reagents