An improved catalyst for the asymmetric arylation of ketone enolates

J Am Chem Soc. 2002 Feb 20;124(7):1261-8. doi: 10.1021/ja011122+.

Abstract

A new catalyst system for the enantioselective alpha-arylation of ketones is reported. This catalyst, prepared from Pd(2)(dba)(3) and a bulky dialkylphosphino-binaphthyl ligand, is able to effect the asymmetric arylation of ketone enolates with aryl bromides utilizing NaO(t)()Bu as base. These new catalysts enjoy much higher reactivity than previous systems; arylation reactions could be effected at room temperature with only 2 mol % of the Pd catalyst. The coupling of alpha-alkyl-alpha'-protected cyclopentanones proceeded in high yield, and the resulting quaternary stereogenic center was installed in up to 94% ee.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Catalysis
  • Cyclopentanes / chemical synthesis
  • Hydrocarbons, Aromatic / chemical synthesis*
  • Ketones / chemical synthesis*
  • Molecular Conformation
  • Organometallic Compounds / chemistry
  • Palladium / chemistry
  • Stereoisomerism

Substances

  • Cyclopentanes
  • Hydrocarbons, Aromatic
  • Ketones
  • Organometallic Compounds
  • cyclopentanone
  • Palladium