Tandem anionic 5-Exo dig cyclization/Claisen rearrangement as an efficient route to fused polycyclic ring systems.

Tandem anionic 5-Exo dig cyclization/Claisen rearrangement as an efficient route to fused polycyclic ring systems.
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串联阴离子 5-Exo dig 环化/克莱森重排是稠合多环系统的有效途径。

DOI:
10.1021/ol006139w
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发表时间:
2000
期刊:
影响因子:
5.2
通讯作者:
Roses,JB
Roses,JB
中科院分区:
化学1区
文献类型:
--
作者:
Ovaska,TV;Roses,JB

文献摘要

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描述了串联5-exo - dig环化/Claisen重排序列的范围和局限性,该序列涉及适当取代的4-炔-1-醇,作为一种有效的“一锅”路线,以融合三环体系。研究发现,反应速率与三键末端取代基的性质密切相关。在某些情况下,整个序列在低至115°C的温度下也能获得良好的产量。
The scope and limitations of a tandem 5-exo dig cyclization/Claisen rearrangement sequence involving appropriately substituted 4-alkyn-1-ols as an efficient “one-pot” route to fused tricyclic ring systems is described. The reaction rates were found to be strongly dependent on the nature of the terminal substitutent of the triple bond. In some cases the entire sequence was found to proceed in good yield at temperatures as low as 115 °C.