取代吲哚与氧代烯丙基阳离子之间的脱芳构化（3+2）环化反应的选择性规则
Selectivity Rules for the Dearomative (3+2) Annulation Reaction Between Substituted Indoles and Oxyallyl Cations.
作者信息
Saha Dhiman, Wu Jimmy
机构信息
Department of Chemistry, Dartmouth College, 41 College St., Hanover, NH 03755, USA.
出版信息
Adv Synth Catal. 2025 Apr 1;367(7). doi: 10.1002/adsc.202401536. Epub 2025 Feb 26.
Abstract
We report a collection of "selectivity rules" for the dearomative (3+2) annulation reaction between substituted indoles and oxyallyl cations. The application of these rules enables us to synthesize four different regioisomeric permutations of the annulation products in a stereoselective fashion. We demonstrated that these products could be further transformed into hexahydro- and tetrahydrocarbazoles by nucleophile-intercepted Beckmann fragmentation (NuBFr) and Beckmann fragmentation (BFr).
摘要
我们报道了一系列关于取代吲哚与氧化烯丙基阳离子之间的去芳构化（3+2）环化反应的“选择性规则”。应用这些规则使我们能够以立体选择性的方式合成环化产物的四种不同区域异构体排列。我们证明，这些产物可以通过亲核试剂截获的贝克曼碎片化反应（NuBFr）和贝克曼碎片化反应（BFr）进一步转化为六氢咔唑和四氢咔唑。
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