Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes

J Am Chem Soc. 2013 Jun 5;135(22):8201-4. doi: 10.1021/ja4047069. Epub 2013 May 23.

Abstract

Rh(I) carbenes were conveniently generated from readily available ynamides. These metal carbene intermediates could undergo metathesis with electron-rich or neutral alkynes to afford 2-oxopyrrolidines or be trapped by tethered alkenes to yield 3-azabicyclo[3.1.0]hexanes, a common skeleton in numerous bioactive pharmaceuticals. Although the scope of the former is limited, the latter reaction tolerates various substituted alkenes.

Publication types

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

MeSH terms

  • Alkenes / chemistry*
  • Alkynes / chemistry*
  • Amides / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Rhodium / chemistry*

Substances

  • Alkenes
  • Alkynes
  • Amides
  • Organometallic Compounds
  • carbene
  • Rhodium
  • Methane