Iridium-catalyzed hydrogenation of β-dehydroamino acid derivatives using monodentate phosphoramidites

Stephan Enthaler, Giulia Erre, Kathrin Junge, Kristin Schröder, Daniele Addis, Dirk Michalik, Marko Hapke, Dmitry Redkin, Matthias Beller

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

The iridium-catalyzed asymmetric hydrogenation of 13 different β-dehydroamino acid derivatives to give optically active β-amino acid esters has been examined. Readily accessible monodentate octahydrobinaphthol- based phosphoramidites were used as chiral ligands. Good to excellent enantioselectivities and yields were obtained for the E isomers, whereas poorer catalyst performance was found for the Z isomers. Importantly, to obtain high enantioselectivity, substitution at the 3,3′-positions of the ligands was necessary. Enantioselectivities of up to 94% ee were achieved under optimized conditions.

Original languageEnglish
Pages (from-to)3352-3362
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number19
DOIs
StatePublished - Jul 2008
Externally publishedYes

Keywords

  • Amino acids
  • Asymmetric catalysis
  • Homogeneous catalysis
  • Hydrogenation
  • Iridium
  • P ligands

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