Enantioselective direct aldol addition of acetone to aliphatic aldehydes

György Szöllosi, Gabor London, Lajos Baláspiri, Csaba Somlai, Mihály Bartók

Research output: Contribution to journalArticle

64 Citations (Scopus)

Abstract

The asymmetric direct aldol addition of acetone to aliphatic aldehydes catalyzed by D-proline, L-proline, and its derivatives was studied. While excellent results could be obtained in neat acetone using α-branched aldehydes, unbranched and β-branched aldehydes gave moderate results. Two dipeptide derivatives, L-Pro-L-Try-CH2OH and L-Pro-L-Trp-OCH3, were prepared and tested in this reaction and both were found to be able to induce enantioselectivities. The ee-values in the case of some aldehydes approached that obtained with L-proline. Immobilization of L-proline on a polystyrene resin by its carboxylic group provided a catalyst which is able to induce enantioselectivity, can be easily removed from the reaction mixture, and reused without a significant decrease in the enantioselectivity of the β-hydroxyketones obtained in the cross-aldol additions.

Original languageEnglish
Pages (from-to)S90-S96
JournalChirality
Volume15
Issue numberSUPPL.
DOIs
Publication statusPublished - Aug 12 2003

Keywords

  • Acetone
  • Aliphatic aldehydes
  • Asymmetric direct aldol addition
  • Immobilization
  • Proline
  • Resin
  • β-hydroxyketones

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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