Enantioselective synthesis of beta2-amino acids using rhodium-catalyzed hydrogenation

Org Biomol Chem. 2007 Jan 21;5(2):267-75. doi: 10.1039/b615131k. Epub 2006 Dec 8.

Abstract

A series of protected beta2-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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Catalysis
  • Chemistry, Organic / methods
  • Hydrogen / chemistry*
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Peptides / chemistry
  • Rhodium / chemistry*
  • Stereoisomerism
  • Temperature

Substances

  • Alcohols
  • Amino Acids
  • Ligands
  • Peptides
  • Hydrogen
  • Rhodium