We herein report the serendipitous discovery of the interrupted Plancher rearrangement initiated by an HFIP-promoted dearomative epoxide–indole cyclization, unlocking a new blueprint to the formal C3 umpolung reactivity of indoles. This rapid complexity generating cascade process paves the way toward a new class of fused–bridged indolines in high yields and under full regio- and diastereocontrol. The reaction is amenable to a wide range of substituents in the starting materials.

中文翻译：

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由脱哚环氧化物-吲哚环化引发的中断 Plancher 重排：吲哚的正式 umpolung 反应性


我们在此报告了由 HFIP 促进的脱氧环氧化物-吲哚环化引发的中断 Plancher 重排的偶然发现，为吲哚的正式 C3 umpolung 反应性解锁了新的蓝图。这种快速产生复杂性的级联工艺为一类新型熔融桥吲哚啉铺平了道路，这些吲哚啉产量高，并且完全区域和非对映控制。该反应适用于起始材料中的多种取代基。