Polyene cyclization promoted by the cross-conjugated α-carbalkoxy enone system. Observation on a putative 1,5-hydride/1,3-alkyl shift under lewis acid catalysis

Ho Hsuan Chou, Huang Min Wu, Jen Dar Wu, Tai Wei Ly, Ning Wei Jan, Kak Shan Shia, Hsing Jang Liu

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15 Citations (Scopus)

Abstract

Polyene cyclization of compounds 3 and 4 under catalysis with AlCl 3 and/or SnCl4 gave rise to complex bicyclic products 8 and 9, structures of which were highly unexpected, and X-ray analyses were invoked for unambiguously structural identification. Mechanistically, a tandem σ-bond rearrangement process, including an unusual through-space 1,5-hydride or 1,3-alkyl shift as a key operation, is proposed.

Original languageEnglish
Pages (from-to)121-123
Number of pages3
JournalOrganic Letters
Volume10
Issue number1
DOIs
Publication statusPublished - 2008 Jan 3

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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