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

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

Research output: Contribution to journalArticle

20 Citations (Scopus)

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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Bearings (structural)
Lewis Acids
Cycloaddition
Cycloaddition Reaction
Cations
lithium aluminum hydride

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Intramolecular 4+3 cycloadditions. A cyclohexenyl cation, its halogenated congener and a quasi-Favorskii rearrangement. / Harmata, Michael; Bohnert, Gary; Kürti, Laszlo; Barnes, Charles L.

In: Tetrahedron Letters, Vol. 43, No. 13, 25.03.2002, p. 2347-2349.

Research output: Contribution to journalArticle

Harmata, Michael ; Bohnert, Gary ; Kürti, Laszlo ; Barnes, Charles L. / Intramolecular 4+3 cycloadditions. A cyclohexenyl cation, its halogenated congener and a quasi-Favorskii rearrangement. In: Tetrahedron Letters. 2002 ; Vol. 43, No. 13. pp. 2347-2349.
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