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Lewis Acid‐Catalyzed Annulation of Propargylic Alcohols with (Z)‐2‐Styryl‐1H‐Indoles
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-10-08 , DOI: 10.1002/adsc.201800907
Xue-Song Li 1 , Ya-Ping Han 1 , Xin-Yu Zhu 1 , Yu Xia 1 , Wan-Xu Wei 1 , Ming Li 1 , Yong-Min Liang 1
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A novel copper(II) trifluoromethanesulfonate‐catalyzed intermolecular cascade annulation strategy for the construction of a great variety of pentacyclic compounds possessing valuable carbazole fragments was developed employing propargylic alcohols and (Z)‐2‐styryl‐1H‐indoles as the initial substrates. This protocol, which entails a sequential Meyer‐Schuster rearrangement/isomerization/‐cyclization cascade, enables facile and atom‐economical access to various pentacyclic compounds with broad functional‐group tolerance in good yields under mild conditions. The conversion could be efficiently scaled up to gram quantities, accentuating a potential application of this work.

中文翻译:

路易斯酸(Z)-2-苯乙烯基-1H-吲哚催化脯氨酸的环化反应

以丙醇和(Z)-2-苯乙烯基-1H-吲哚为初始底物,开发了一种新颖的三氟甲磺酸铜(II)催化的分子间级联环化策略,用于构建多种具有有价值的咔唑片段的五环化合物。该方案需要进行连续的Meyer-Schuster重排/异构化/环化级联反应,可在温和条件下轻松,原子经济地获得具有宽泛官能团耐受性的五环化合物,并具有良好的收率。转换可以有效地按比例放大至克数量,从而加重了这项工作的潜在应用范围。
更新日期:2018-10-08
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