A general copper-BINAP-catalyzed asymmetric propargylation of ketones with propargyl boronates

J Am Chem Soc. 2011 Jul 13;133(27):10332-5. doi: 10.1021/ja2028958. Epub 2011 Jun 22.

Abstract

An operationally simple copper-BINAP-catalyzed, highly enantioselective propargylation of ketones is presented. The methodology was developed as an enantioselective process for methyl ethyl ketone and shown to be applicable to a wide variety of prochiral ketones. The resulting homopropargyl adducts are versatile latent carbonyls from which γ-butyrolactones, β-hydroxy methyl ketones, and β-hydroxycarboxylates are readily obtained.

MeSH terms

  • Boronic Acids / chemistry*
  • Butanones / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Ketones / chemistry*
  • Naphthalenes / chemistry*
  • Pargyline / chemistry

Substances

  • BINAP, 2-naphthol
  • Boronic Acids
  • Butanones
  • Ketones
  • Naphthalenes
  • methylethyl ketone
  • Copper
  • Pargyline