Organocatalytic Asymmetric Aldol Reaction of Arylglyoxals and Hydroxyacetone: Enantioselective Synthesis of 2,3-Dihydroxy-1,4-diones

Molecules. 2020 Feb 3;25(3):648. doi: 10.3390/molecules25030648.

Abstract

A highly efficient quinine-derived primary-amine-catalyzed asymmetric aldol addition of hydroxyacetone to arylglyoxals is described. Structurally diverse anti-2,3-dihydroxy-1,4-diones were generated in high yields, with good diastereoselectivities and enantioselectivities.

Keywords: 2,3-Dihydroxy-1,4-dione; aldol reaction; arylglyoxal; asymmetric synthesis; organocatalysis.

MeSH terms

  • Acetone / analogs & derivatives*
  • Acetone / chemistry
  • Aldehydes / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Glyoxylates / chemistry*
  • Molecular Structure

Substances

  • Aldehydes
  • Glyoxylates
  • Acetone
  • acetol
  • 3-hydroxybutanal
  • glyoxylic acid