Lewis acid-catalyzed asymmetric diels-alder reactions using chiral sulfoxide ligands: chiral 2-(arylsulfinylmethyl)-1,3-oxazoline derivatives

Chem Pharm Bull (Tokyo). 2002 Mar;50(3):372-9. doi: 10.1248/cpb.50.372.

Abstract

New chiral sulfoxide-1,3-oxazoline ligands have been developed as chiral ligands for Lewis acid-catalyzed asymmetric Diels-Alder reactions. The use of chiral sulfinyl 1,3-oxazoline ligands in copper(II)-catalyzed asymmetric Diels-Alder reactions provided an endo cycloadduct as a major product with moderate enantioselectivity. A rationale is proposed for the mechanism of the asymmetric induction.

MeSH terms

  • Acids / chemistry*
  • Catalysis
  • Oxazoles / chemistry*
  • Spectrum Analysis
  • Stereoisomerism
  • Sulfoxides / chemistry*

Substances

  • Acids
  • Oxazoles
  • Sulfoxides