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Synlett
DOI: 10.1055/a-2718-1886
DOI: 10.1055/a-2718-1886
Letter
N-Heterocyclic Carbene-Catalyzed Acylalkylation of Indole via C–C Bond Cleavage/Dearomatization to Access the Multisubstituted Benzopyrrolizidinones
Authors
Funding Information The authors gratefully acknowledge the Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province (CSPC201907), Asymmetric Synthesis and Chirotechnology Key Laboratory of Sichuan Province (2024KFKT04), Vanadium and Titanium Resource Comprehensive Utilization Key Laboratory of Sichuan Province (No. 2020FTSZ09), the College Students’ Innovation and the Entrepreneurship Training Program of Sichuan University of Science & Engineering (cx2025050), National Natural Science Foundation of China (22373056), the Innovation Projects of Department of Education of Guangdong Province (2023KTSCX135), the Scientific Research and Innovation Team Program of Sichuan University of Science and Engineering (SUSE652A014), the “Hundreds of Counties, Thousands of Towns, and Myriads of Villages” Project of Shaoguang City in 2024 for financial support.
Abstract
The development of novel approaches to construct benzopyrrolizidinones skeleton under metal-free conditions remains a significant challenge in medicinal chemistry. Therefore, we report an efficient methodology for construction of multisubstituted benzopyrrolizidinones via N-heterocyclic carbene-catalyzed acylalkylation reactions of indoles, involving C–C bond cleavage and dearomatization. This method exhibits the broad scope, excellent diastereoselectivity, allowing for formation of multisubstituted benzopyrrolizidinones under mild conditions. Moreover, N-heterocyclic carbene-catalyzed acylalkylation of Indole was further applied to the late-stage functionalization of pharmaceutical skeletons.
Publication History
Received: 26 August 2025
Accepted after revision: 07 October 2025
Accepted Manuscript online:
07 October 2025
Article published online:
06 November 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
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