Synthesis of non-symmetric bis(oxazoline)-containing ligands and their application in the catalytic enantioselective Nozaki-Hiyama-Kishi allylation of benzaldehyde

Org Biomol Chem. 2008 Feb 7;6(3):562-6. doi: 10.1039/b715834c. Epub 2007 Dec 20.

Abstract

We report the good to high-yielding three-step synthesis of non-symmetrical bis(oxazoline)-containing ligands possessing an N-thienylaniline unit. The convergent synthesis employed a palladium-catalysed aryl amination of 2-(2'-bromothiophene)nitrile as the key step, with sixteen ligands prepared in total. These ligands were subsequently applied in the chromium-catalysed enantioselective Nozaki-Hiyama-Kishi allylation of benzaldehyde with an optimal enantioselectivity of 73%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry
  • Benzaldehydes / chemistry*
  • Catalysis
  • Chromium / chemistry
  • Ligands
  • Palladium / chemistry
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Aniline Compounds
  • Benzaldehydes
  • Ligands
  • Chromium
  • Palladium
  • aniline
  • benzaldehyde