Enantioselective Friedel-Crafts reactions in water using a DNA-based catalyst

Angew Chem Int Ed Engl. 2009;48(18):3346-8. doi: 10.1002/anie.200900371.

Abstract

Taking the plunge: The first example of a Lewis acid catalyzed asymmetric Friedel-Crafts alkylation with olefins in water is described. By using loadings of a DNA-based copper catalyst as low as 0.15 mol %, good yields and excellent enantioselectivities were obtained in the reaction of alpha,beta-unsaturated 2-acyl imidazoles with heteroaromatic pi nucleophiles. dmbpy = 4,4'-dimethyl-2,2'-bipyridine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Alkylation
  • Catalysis
  • Copper / chemistry*
  • DNA / chemistry*
  • Imidazoles / chemistry*
  • Stereoisomerism
  • Water / chemistry*

Substances

  • Alkenes
  • Imidazoles
  • Water
  • Copper
  • DNA