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

doi:10.1021/ol702631q

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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17 引文斯高帕斯（Scopus）

摘要

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.

原文	English
頁（從 - 到）	121-123
頁數	3
期刊	Organic Letters
卷	10
發行號	1
DOIs	https://doi.org/10.1021/ol702631q
出版狀態	Published - 2008 1月 3

All Science Journal Classification (ASJC) codes

生物化學
物理與理論化學
有機化學

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10.1021/ol702631q

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title = "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",

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.",

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doi = "10.1021/ol702631q",

language = "English",

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T1 - 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

AU - Chou, Ho Hsuan

AU - Wu, Huang Min

AU - Wu, Jen Dar

AU - Ly, Tai Wei

AU - Jan, Ning Wei

AU - Shia, Kak Shan

AU - Liu, Hsing Jang

PY - 2008/1/3

Y1 - 2008/1/3

N2 - 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.

AB - 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.

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U2 - 10.1021/ol702631q

DO - 10.1021/ol702631q

M3 - Article

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JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 1

ER -

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

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