Control of olefin geometry in macrocyclic ring-closing metathesis using a removable silyl group

J Am Chem Soc. 2011 Jun 22;133(24):9196-9. doi: 10.1021/ja202012s. Epub 2011 May 27.


Introducing a silyl group at one of the internal olefin positions in diolefinic substrates results in E-selective olefin formation in macrocyclic ring-forming metathesis. The application of this method to a range of macrocyclic (E)-alkenylsiloxanes is described. Protodesilylation of alkenylsiloxane products yields novel Z-configured macrocycles.

Publication types

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

MeSH terms

  • Alkenes / chemistry*
  • Macrocyclic Compounds / chemistry*
  • Silanes / chemistry*
  • Stereoisomerism
  • Substrate Specificity


  • Alkenes
  • Macrocyclic Compounds
  • Silanes