Formation of hydrindans and tricyclo[4.3.0.03,8]nonanes via 6-endo trapping of the Nazarov oxyallyl intermediate

C. C. Browder, F. G. West

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

Treatment of trienones 1a-g with BF3·OEt2 at -78°C followed by warming effected Nazarov electrocyclization followed by 6-endo cation-olefin cyclization. The resulting tertiary carbocations underwent elimination to give olefinic products 2, intramolecular hydride transfer to furnish enones 3 and/or 3+2 ring-closure providing tricyclic products 4. Use of TiCl4 in place of BF3·OEt2 led in most cases to a mixture of enones 3 and chloride- trapping products 7.

Original languageEnglish (US)
Pages (from-to)1363-1366
Number of pages4
JournalSynlett
Issue number9
DOIs
StatePublished - Jan 1 1999
Externally publishedYes

Keywords

  • Cyclizations
  • Domino reactions
  • Polycycles
  • Ring closure
  • Tandem reactions

ASJC Scopus subject areas

  • Organic Chemistry

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