Proline-beta(3)-amino-ester dipeptides as efficient catalysts for enantioselective direct aldol reaction in aqueous medium

J Org Chem. 2009 Dec 18;74(24):9562-5. doi: 10.1021/jo902106r.

Abstract

Dipeptides obtained from l-proline and beta(3)-l-amino acids are reported to catalyze enantioselective direct aldol reaction in aqueous medium, leading to significant anti:syn diastereomeric ratios and enantiomeric excesses. The simple introduction of a polar substituent at the C-2 position of the beta(3)-l-amino acid was also found to enhance appreciably both diastereo- and enantioselectivity of the catalyst.

MeSH terms

  • Aldehydes / chemistry*
  • Benzaldehydes / chemistry
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Cyclohexanones / chemistry
  • Dipeptides / chemistry*
  • Esters / chemistry*
  • Hydrophobic and Hydrophilic Interactions
  • Magnetic Resonance Spectroscopy
  • Proline / analogs & derivatives
  • Proline / chemistry*
  • Stereoisomerism
  • Tryptophan / analogs & derivatives
  • Tryptophan / chemistry
  • Tyrosine / analogs & derivatives
  • Tyrosine / chemistry
  • Water / chemistry*

Substances

  • Aldehydes
  • Benzaldehydes
  • Cyclohexanones
  • Dipeptides
  • Esters
  • Water
  • Tyrosine
  • 4-nitrobenzaldehyde
  • cyclohexanone
  • 3-hydroxybutanal
  • Tryptophan
  • Proline