1-Vinyl-4-methyl-2,6,7-trioxabicyclo[2.2.2]octanes: Unsaturated homoenolate anion equivalents

Stewart K. Richardson, Alwarsamy Jeganathan, David S. Watt

Research output: Contribution to journalArticlepeer-review

19 Scopus citations


The metalation of (E)-1-(2-chlorovinyl)- or (E)-1-(2-bromovinyl)-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane with tert-butyllithium produced an unsaturated homoenolate anion equivalent which intercepted alkyl halides, aldehydes, ketones, and lactones to afford β-alkylated or β-acylated orthoesters, which, in turn, furnished β-substituted acrylate esters.

Original languageEnglish
Pages (from-to)2335-2338
Number of pages4
JournalTetrahedron Letters
Issue number21
StatePublished - 1987

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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