Enantioselective synthesis of beta(2)-amino acids using rhodium-catalyzed hydrogenation

Rob Hoen, Theodora Tiemersma-Wegman, Barbara Procuranti, Laurent Lefort, Johannes G. de Vries, Adriaan J. Minnaard*, Ben L. Feringa

*Corresponding author for this work

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Abstract

A series of protected beta(2)-dehydroamino acids has been prepared in three steps from commercially available starting materials in good yields. These were used as substrates in rhodium-catalyzed asymmetric hydrogenation applying a mixed ligand system of monodentate phosphoramidites and phosphines. Optimization of the catalyst structure was achieved by high throughput experimentation. High enantioselectivities were obtained ( up to 91%) with full conversion for a number of beta-amino acids.

Original languageEnglish
Pages (from-to)267-275
Number of pages9
JournalOrganic & Biomolecular Chemistry
Volume5
Issue number2
DOIs
Publication statusPublished - 2007

Keywords

  • MONODENTATE P-LIGANDS
  • BETA-AMINO ACIDS
  • TRANSITION-METAL CATALYSIS
  • ASYMMETRIC HYDROGENATION
  • COMBINATORIAL APPROACH
  • OLEFIN-HYDROGENATION
  • PHOSPHORAMIDITE LIGANDS
  • STEREOSELECTIVE-SYNTHESIS
  • ABSOLUTE-CONFIGURATION
  • PHOSPHORUS LIGANDS

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