Chemoselective catalytic conjugate addition of alcohols over amines

Angew Chem Int Ed Engl. 2014 Feb 3;53(6):1611-5. doi: 10.1002/anie.201309755. Epub 2014 Jan 22.

Abstract

A highly chemoselective conjugate addition of alcohols in the presence of amines is described. The cooperative nature of the catalyst enabled chemoselective activation of alcohols over amines, allowing the conjugate addition to soft Lewis basic α,β-unsaturated nitriles. Divergent transformation of the nitrile functionality highlights the utility of the present catalysis.

Keywords: amino alcohols; chemoselective catalysis; cooperative effects; proton transfer; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Amines / chemistry*
  • Catalysis
  • Lewis Bases / chemistry
  • Nitriles / chemistry
  • Protons

Substances

  • Alcohols
  • Amines
  • Lewis Bases
  • Nitriles
  • Protons