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

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

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 skelet...

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Bibliographic Details
Published in:Organic letters Vol. 25; no. 21; pp. 3829 - 3834
Main Authors: Zheng, Jianfeng, Yang, Lin, Dai, Xin, Chen, Lvli, Tang, Luhao, Zhou, Yuqiao, Li, Wei-Dong Z.
Format: Journal Article
Language:English
Published: United States American Chemical Society 02-06-2023
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01085