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Diastereodivergent Synthesis of Pentacyclic Spiroindolines via a Magnesium(II)-Catalyzed Cascade Reaction of N,N'-Cyclic Azomethine Imines with Indolyl-Substituted Isocyanides.

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Magnesium(II)-catalyzed cascade reactions of N,N'-cyclic azomethine imines with indolyl-substituted isocyanides are reported herein. The method exhibited a high functional group tolerance and broad substrate scope. A series of anti-pentacyclic spiroindolines… Click to show full abstract

Magnesium(II)-catalyzed cascade reactions of N,N'-cyclic azomethine imines with indolyl-substituted isocyanides are reported herein. The method exhibited a high functional group tolerance and broad substrate scope. A series of anti-pentacyclic spiroindolines containing N,N'-fused heterocycle skeletons were obtained in up to 82% yield with 8.5:1 dr under mild reaction conditions. Intriguingly, a sequential HOAc-mediated protonation results in a diastereoenriched epimerization, which gives rise to the syn-pentacyclic spiroindolines as the sole isomers.

Keywords: azomethine imines; pentacyclic spiroindolines; catalyzed cascade; imines indolyl; cyclic azomethine; magnesium catalyzed

Journal Title: Organic letters
Year Published: 2023

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