Stereocontrolled regeneration of olefins from epoxides

Veronica S. Wills, Xiang Zhou, Cheryl Allen, Sarah A. Holstein, David F. Wiemer

Research output: Contribution to journalArticlepeer-review

4 Scopus citations


Through treatment with NaI and trifluoroacetic anhydride, which presumably forms trifluoroacetyl iodide in situ, epoxides can be converted to olefins. This reaction now has been shown to tolerate remote olefins without loss of their individual stereochemistry. A reaction sequence involving regiospecific epoxidation of an isoprenoid alcohol, conversion of the alcohol to an azide, and cycloaddition with an acetylene, followed by conversion of the epoxide back to the original olefin, has allowed stereocontrolled preparation of triazole bisphosphonates with a farnesyl or a geranylgeranyl substituent. This strategy may be applicable for selective protection of an alkene in other polyolefins, including substrates for metathesis reactions.

Original languageEnglish (US)
Pages (from-to)1335-1337
Number of pages3
JournalTetrahedron Letters
Issue number12
StatePublished - Mar 23 2016
Externally publishedYes


  • Deoxygenation
  • Epoxide
  • Phosphonate
  • Triazole

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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