A cyclization-rearrangement cascade for the synthesis of structurally complex chiral gold(I)-aminocarbene complexes

Angew Chem Int Ed Engl. 2014 Jul 28;53(31):8122-6. doi: 10.1002/anie.201403651. Epub 2014 Jul 7.

Abstract

A facile synthesis of chiral cyclic alkyl aminocarbene-gold(I) complexes from gold-free 1,7-enyne substrates was developed. The novel cyclization-rearrangement reaction sequence is triggered by the addition of (Me2S)AuCl to different 1,7-enynes and leads to structurally unique carbene-gold(I) complexes in high yields. These novel complexes are catalytically active and inhibit the proliferation of different human cancer cell lines.

Keywords: carbenes; cyclization; enynes; organometallic complexes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Cyclization*
  • Dioxolanes / chemistry*
  • Gold / chemistry*
  • Stereoisomerism

Substances

  • Alkynes
  • Dioxolanes
  • aminocarbene
  • Gold