Intramolecular 4+3 cycloadditions. A cyclohexenyl cation, its halogenated congener and a quasi-Favorskii rearrangement

Michael Harmata, Gary Bohnert, Laszlo Kürti, Charles L. Barnes

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Abstract

Treatment of alkoxycyclohexenols bearing a tethered diene substituent with a Lewis acid results in intramolecular 4+3 cycloaddition with complete endo selectivity. A cycloadduct bearing a bromo substituent at a bridgehead position undergoes a quasi-Favorskii rearrangement in near quantitative yield upon reaction with lithium aluminum hydride.

Original languageEnglish (US)
Pages (from-to)2347-2349
Number of pages3
JournalTetrahedron Letters
Volume43
Issue number13
DOIs
StatePublished - Mar 25 2002

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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