Enantioselective ruthenium-catalyzed carbonyl allylation via alkyne-alcohol C-C bond-forming transfer hydrogenation: allene hydrometalation vs oxidative coupling

J Am Chem Soc. 2015 Mar 11;137(9):3161-4. doi: 10.1021/jacs.5b00747. Epub 2015 Mar 3.

Abstract

Chiral ruthenium(II) complexes modified by Josiphos ligands catalyze the reaction of alkynes with primary alcohols to form homoallylic alcohols with excellent control of regio-, diastereo-, and enantioselectivity. These processes represent the first examples of enantioselective carbonyl allylation using alkynes as allylmetal equivalents.

Publication types

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

MeSH terms

  • Alcohols / chemistry*
  • Alkadienes / chemistry*
  • Alkynes / chemistry*
  • Allyl Compounds / chemistry
  • Catalysis
  • Hydrogenation
  • Oxidation-Reduction
  • Ruthenium / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Alkadienes
  • Alkynes
  • Allyl Compounds
  • propadiene
  • Ruthenium