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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

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 σ-bond rearrangement pro...

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Bibliographic Details
Published in:Organic letters 2008-01, Vol.10 (1), p.121-123
Main Authors: Chou, Ho-Hsuan, Wu, Huang-Min, Wu, Jen-Dar, Ly, Tai Wei, Jan, Ning-Wei, Shia, Kak-Shan, Liu, Hsing-Jang
Format: Article
Language:English
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Summary: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 σ-bond rearrangement process, including an unusual through-space 1,5-hydride or 1,3-alkyl shift as a key operation, is proposed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702631q