Selective access to trisubstituted macrocyclic E- and Z-alkenes from the ring-closing metathesis of vinylsiloxanes

Org Lett. 2013 Mar 15;15(6):1218-21. doi: 10.1021/ol400134d. Epub 2013 Feb 28.


Macrocyclic (E)-alkenylsiloxanes, obtained from E-selective ring-closing metathesis reactions, can be converted to the corresponding (Z)-alkenyl bromides and (E)-alkenyl iodides allowing access to both E- and Z-trisubstituted macrocyclic alkenes. The reaction conditions and substrate scope of these stereoselective transformations are explored.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Catalysis
  • Chemistry, Organic / methods
  • Cyclization
  • Hydrocarbons, Halogenated / chemical synthesis*
  • Hydrocarbons, Halogenated / chemistry
  • Molecular Structure
  • Siloxanes / chemistry*
  • Stereoisomerism


  • Alkenes
  • Hydrocarbons, Halogenated
  • Siloxanes