Divergent Asymmetric Synthesis of Polycyclic Spiroindolines via Cascade Cycloadditions

Comprehensive Summary The asymmetric construction of polycyclic spiroindolines featuring one or more quaternary stereocenters remains a significant challenge in synthetic chemistry. We report a highly chemoselective and stereoselective cascade cycloadditions of newly designed oxazepino indolones with 5‐methylene‐1,3‐dioxanones, employing an iridium catalyst in combination with the Carreira ligand for the divergent synthesis of chiral polycyclic spiroindolines. This strategy enables the construction of a series of pentacyclic spiroindolines featuring two chiral quaternary stereocenters and one tertiary stereocenter in good yields with excellent chemoselectivity and stereocontrol (30 examples, up to 81% yield, >20 : 1 dr, 99% ee ). The process was scalable, and synthetic transformations of the products were performed to demonstrate their practical utility.

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Publication Details

Journal
Chinese Journal of Chemistry
Published
2025-08-08
DOI
https://doi.org/10.1002/cjoc.70191
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Divergent Asymmetric Synthesis of Polycyclic Spiroindolines via Cascade Cycloadditions

Xiaoxun Li, Fuxing Yin, Peifang Lu, Yu Jiang et al.
Chinese Journal of Chemistry
Asymmetric Synthesis and Catalysis
article

Divergent Asymmetric Synthesis of Polycyclic Spiroindolines via Cascade Cycloadditions

Xiaoxun Li, Fuxing Yin, Peifang Lu, Yu Jiang, Jitian Liu, Huan Zhang, Jianhua Wang, Chenchen Ma, J. P. Du
article en

Abstract

Comprehensive Summary The asymmetric construction of polycyclic spiroindolines featuring one or more quaternary stereocenters remains a significant challenge in synthetic chemistry. We report a highly chemoselective and stereoselective cascade cycloadditions of newly designed oxazepino indolones with 5‐methylene‐1,3‐dioxanones, employing an iridium catalyst in combination with the Carreira ligand for the divergent synthesis of chiral polycyclic spiroindolines. This strategy enables the construction of a series of pentacyclic spiroindolines featuring two chiral quaternary stereocenters and one tertiary stereocenter in good yields with excellent chemoselectivity and stereocontrol (30 examples, up to 81% yield, >20 : 1 dr, 99% ee ). The process was scalable, and synthetic transformations of the products were performed to demonstrate their practical utility.

Chinese Journal of ChemistryVol. 43(23)
Shandong University of Traditional Chinese Medicine (CN), Shandong University (CN), Jinan Central Hospital (CN), Suzhou Research Institute (CN), Jining First People's Hospital (CN), Affiliated Hospital of Shandong University of Traditional Chinese Medicine (CN), Shandong First Medical University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Shandong Province
Openalex Percentile: Top 84%
Asymmetric Synthesis and Catalysis
DOIOpen Access PDFOpenAlex
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Divergent Asymmetric Synthesis of Polycyclic Spiroindolines via Cascade Cycloadditions — Xiaoxun Li, Fuxing Yin, et al. · Chinese Journal of Chemistry (2025) | TGRS Research Map | TGRS