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  • Title: Polyene cyclization promoted by the cross-conjugated alpha-carbalkoxy enone system. Observation on a putative 1,5-hydride/1,3-alkyl shift under Lewis acid catalysis.
    Author: Chou HH, Wu HM, Wu JD, Ly TW, Jan NW, Shia KS, Liu HJ.
    Journal: Org Lett; 2008 Jan 03; 10(1):121-3. PubMed ID: 18052186.
    Abstract:
    Polyene cyclization of compounds 3 and 4 under catalysis with AlCl3 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 sigma-bond rearrangement process, including an unusual through-space 1,5-hydride or 1,3-alkyl shift as a key operation, is proposed.
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