Diastereo- and enantioselective propargylation of benzofuranones catalyzed by pybox-copper complex

Org Lett. 2014 Nov 7;16(21):5584-7. doi: 10.1021/ol502615y. Epub 2014 Oct 17.

Abstract

Diastereo- and enantioselective preparation of 2,2-disubstituted benzofuran-3(2H)-one has been realized by a pybox-copper catalyzed reaction between 2-substituted benzofuran-3(2H)-one and propargyl acetate. The utility of this method was demonstrated by further transformation of the terminal alkyne into a methyl ketone without loss of enantiomeric purity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Benzofurans / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry*
  • Molecular Structure
  • Pargyline / analogs & derivatives
  • Pargyline / chemistry*
  • Stereoisomerism

Substances

  • Alkynes
  • Benzofurans
  • Ketones
  • Copper
  • Pargyline