Glucosamine-based primary amines as organocatalysts for the asymmetric aldol reaction

J Org Chem. 2011 May 6;76(9):3502-5. doi: 10.1021/jo1023156. Epub 2011 Mar 21.

Abstract

Glucosamine derivatives have been synthesized starting from commercially available N-acetyl-D-glucosamine/glucosamine hydrochloride and have been employed successfully as efficient organocatalysts for the direct asymmetric aldol reaction between cyclohexanone and aryl aldehydes having diversified substituents. Furthermore, the anomeric effect of various groups present at the anomeric position on the catalytic activity of these organocatalysts was also studied.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Amines / chemistry*
  • Catalysis
  • Glucosamine / chemistry*
  • Ketones / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Amines
  • Ketones
  • Glucosamine