Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization - Electrophilic aromatic substitution

Cindy C. Browder, Fredrik P. Marmsäter, F. G. West

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

1,4-Dien-3-ones substituted with pendant arylethyl side chains attached at C-1 were readily prepared from substituted dihydrocinnamaldehydes. Treatment with TiCl4 at low temperature effected domino Nazarov electrocyclization - arene trapping within 5 min to give racemic benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.

Original languageEnglish (US)
Pages (from-to)375-385
Number of pages11
JournalCanadian Journal of Chemistry
Volume82
Issue number2
DOIs
StatePublished - Feb 1 2004

    Fingerprint

Keywords

  • Domino process
  • Electrophilic aromatic substitution
  • Lewis acid
  • Nazarov cyclization

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this