Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes
The asymmetric Büchner reaction and related arene cyclopropanations represent one type of the powerful methods for enantioselective dearomatization. However, examples of asymmetric Büchner reactions via a non-diazo approach are quite scarce, and the related arene cyclopropanation based on alkynes has not been reported. Herein, we disclose an asymmetric Büchner reaction and the related arene cyclopropanation by copper-catalyzed controllable cyclization of N-propargyl ynamides via vinyl cation intermediates, leading to chiral tricycle-fused cycloheptatrienes and benzonorcaradienes in high yields and enantioselectivities. Importantly, this protocol represents an asymmetric arene cyclopropanation reaction of alkynes and an asymmetric Büchner reaction based on vinyl cations.
Authors
- Xin Hong (ORCID: https://orcid.org/0000-0003-4717-2814)
- Long‐Wu Ye (ORCID: https://orcid.org/0000-0003-3108-2611)
- Zhou Xu (ORCID: https://orcid.org/0000-0002-9703-8245)
- Yan-Xin Zheng
- Xin Lü (ORCID: https://orcid.org/0000-0003-4968-9462)
- Li‐Gao Liu (ORCID: https://orcid.org/0000-0001-5002-7429)
- Xiao Li (ORCID: https://orcid.org/0000-0002-5238-6393)
- Bo Zhou (ORCID: https://orcid.org/0000-0002-5551-678X)
- Tian-Qi Hu
Institutions
- Xuzhou Medical College (CN)
- Xiamen University (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Collaborative Innovation Center of Chemistry for Energy Materials (CN)
- State Key Laboratory of Clean Energy Utilization
- Zhejiang University (CN)
Publication Details
- Journal
- Nature Communications
- Published
- 2024-10-25
- DOI
- https://doi.org/10.1038/s41467-024-53605-7
- Citations
- 28
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 7.00
Funders
- National Natural Science Foundation of China
- Government of Jiangsu Province
- Natural Science Foundation of Jiangsu Province
- Zhejiang University
- Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
- Fundamental Research Funds for the Central Universities
- Beijing National Laboratory for Molecular Sciences
- Natural Science Foundation of Zhejiang Province