Asymmetric direct aldol reactions of acetoacetals catalyzed by a simple chiral primary amine

J Org Chem. 2009 Dec 18;74(24):9521-3. doi: 10.1021/jo9021259.

Abstract

An asymmetric direct aldol reaction of acetoacetals is described. Under the catalysis of a simple chiral primary amine, the direct aldol reactions of acetoacetals occur exclusively on the gamma-position to give vinylogous-type aldol products with high diastereo- and enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemistry*
  • Acetates / chemistry*
  • Aldehydes / chemistry*
  • Amines / chemistry*
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Ketones / chemistry
  • Macrolides / chemical synthesis
  • Macrolides / chemistry
  • Magnetic Resonance Spectroscopy
  • Solvents / chemistry
  • Stereoisomerism
  • Vinyl Compounds / chemistry

Substances

  • Acetals
  • Acetates
  • Aldehydes
  • Amines
  • Biological Products
  • Ketones
  • Macrolides
  • Solvents
  • Vinyl Compounds
  • 3-hydroxybutanal