Organocatalytic C─O Bond Cleavage and Asymmetric Transformations via [1,3]‐Sigmatropic Rearrangement
Here, an organocatalytic asymmetric [1,3]-sigmatropic rearrangement process for aryl ether insertion through C─O bond cleavage and downstream transformation is reported, enabling the practical and atom-economic synthesis of diverse valuable chiral benzofuran derivatives bearing a quaternary carbon stereocenter. The reaction shows a wide substrate scope, yielding moderate to good products with excellent enantioselectivity and diastereoselectivity (up to >99% ee and >99:1 d.r.). Initial biological activity tests suggest that the resulting enantioenriched benzofuran products hold potential as anticancer agents.
Authors
- Xuli Feng (ORCID: https://orcid.org/0000-0003-0476-9346)
- Wenling Qin (ORCID: https://orcid.org/0000-0002-5654-5785)
- Jie Zhang (ORCID: https://orcid.org/0000-0001-7528-4077)
- Lina Yin (ORCID: https://orcid.org/0009-0009-4384-6915)
- Yu Chang
- Lei Peng (ORCID: https://orcid.org/0000-0002-9369-9417)
- Hui‐chao Yan (ORCID: https://orcid.org/0000-0002-6073-6824)
- Pengfei Wang (ORCID: https://orcid.org/0000-0002-8233-8798)
Institutions
- Chongqing University (CN)
- Fuling Center Hospital of Chongqing (CN)
Publication Details
- Journal
- Advanced Science
- Published
- 2025-05-19
- DOI
- https://doi.org/10.1002/advs.202504718
- Citations
- 3
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- National Natural Science Foundation of China
- Chongqing University
- Natural Science Foundation of Chongqing
- Fundamental Research Funds for the Central Universities