Combining Enzyme and Photoredox Catalysis for the Construction of 3-Aminoalkyl Chromones

J Org Chem. 2022 Nov 4;87(21):14965-14969. doi: 10.1021/acs.joc.2c01977. Epub 2022 Oct 24.

Abstract

Herein, we reported a practical and efficient strategy combining photoredox and enzyme catalysis for the construction of 3-aminoalkyl chromones from o-hydroxyaryl enaminones and N-arylglycine esters. A variety of 3-aminoalkyl chromones were synthesized with good yields under mild conditions in one pot. This synthetic protocol consists of sequential enzymatic hydrolysis and photoredox decarboxylation of N-arylglycine esters, oxidation of aminoalkyl radicals, Mannich reaction, and intramolecular nucleophilic cyclization, which affords a convenient pathway for the preparation of various 3-substituted chromones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chromones*
  • Cyclization
  • Esters*
  • Oxidation-Reduction

Substances

  • Chromones
  • Esters