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

25 Citations (Scopus)

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 2004
Externally publishedYes

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Substitution reactions
Temperature
titanium tetrachloride

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization - Electrophilic aromatic substitution. / Browder, Cindy C; Marmsäter, Fredrik P.; West, F. G.

In: Canadian Journal of Chemistry, Vol. 82, No. 2, 02.2004, p. 375-385.

Research output: Contribution to journalArticle

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