Catalytic enantioselective C-H functionalization of alcohols by redox-triggered carbonyl addition: borrowing hydrogen, returning carbon

Angew Chem Int Ed Engl. 2014 Aug 25;53(35):9142-50. doi: 10.1002/anie.201403873. Epub 2014 Jul 23.

Abstract

The use of alcohols and unsaturated reactants for the redox-triggered generation of nucleophile-electrophile pairs represents a broad, new approach to carbonyl addition chemistry. Discrete redox manipulations that are often required for the generation of carbonyl electrophiles and premetalated carbon-centered nucleophiles are thus avoided. Based on this concept, a broad, new family of enantioselective C-C coupling reactions that are catalyzed by iridium or ruthenium complexes have been developed, which are summarized in this Minireview.

Keywords: enantioselective catalysis; iridium; polyketide natural products; ruthenium; transfer hydrogenation.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Alcohols / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Hydrogen / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Alcohols
  • Carbon
  • Hydrogen