Development of pinene-derived N,P ligands and their utility in catalytic asymmetric hydrogenation

Dalton Trans. 2007 Dec 21:(47):5603-10. doi: 10.1039/b713257n. Epub 2007 Oct 26.

Abstract

New diastereomeric N,P-ligands, derived from the natural product (+)-alpha-pinene, have been synthesized and evaluated in iridium-catalyzed asymmetric hydrogenation. The ligands are tetrahydroquinoline derivatives synthesized directly from commercially available alpha-pinene utilizing resolution or recrystallization to separate diastereomers. In reduction of a range of different trisubstituted alkenes the catalysts express very different activities ranging from no activity to high activity. One of the catalysts gives good ee values for some substrates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bicyclic Monoterpenes
  • Catalysis
  • Hydrogen / chemistry*
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Monoterpenes / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared

Substances

  • Bicyclic Monoterpenes
  • Ligands
  • Monoterpenes
  • Hydrogen
  • alpha-pinene