Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s.
Lewis acid catalyzed cascade reaction of 3-(2-benzenesulfonamide)propargylic alcohols to spiro[indene-benzosultam]s.
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DOI：
10.1021/ol503316e
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发表时间：
2015-01
期刊：
影响因子：
5.2
通讯作者：
Lang Sun;Yuanxun Zhu;Jing Wang;P. Lu;Yanguang Wang
中科院分区：
文献类型：
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作者：
Lang Sun;Yuanxun Zhu;Jing Wang;P. Lu;Yanguang Wang
以炔丙醇为原料，高效、简便地合成了螺[茚-苯并磺内酰胺]骨架。该反应在刘易斯酸催化的级联过程中进行，包括用磺酰胺捕获丙二烯碳正离子、亲电环化和分子内Friedel-Crafts烷基化。在NIS或NBS存在下，碘/溴取代螺[茚-苯并磺内酰胺]可以以优异的产率制备。
A highly efficient and convenient construction of the spiro[indene-benzosultam] skeleton from propargylic alcohols has been developed. The reaction proceeded in a Lewis acid catalyzed cascade process, including the trapping of allene carbocation with sulfonamide, electrophilic cyclization, and intramolecular Friedel-Crafts alkylation. In the presence of NIS or NBS, iodo/bromo-substituted spiro[indene-benzosultam]s could be prepared in excellent yields.