Synthesis of a tertiary carbinamide via a novel Rh-catalyzed asymmetric hydrogenation

J Org Chem. 2008 Feb 15;73(4):1639-42. doi: 10.1021/jo702429u. Epub 2008 Jan 11.

Abstract

Asymmetric hydrogenation of allylic dimethylcarbinamide 2 with 1 mol % of cationic Rh(I)-Josiphos complex in THF under 500 psi of H2 generated the corresponding tertiary carbinamide 1 in 98.5% assay yield and a 94:6 enantiomeric ratio. Upon crystallization, the product was isolated in 91% isolated yield and 95:5 enantiomeric ratio.

MeSH terms

  • Amides / chemistry*
  • Catalysis
  • Crystallization
  • Hydrogen / chemistry*
  • Magnetic Resonance Spectroscopy
  • Rhenium / chemistry*
  • Spectrophotometry, Infrared

Substances

  • Amides
  • Rhenium
  • Hydrogen