An Unexpected [3 + 2]-Cycloaddition between Spiro-Epoxyoxindoles and γ-Deconjugated Butenolides Catalyzed by Sc(OTf)<sub>3</sub>
A unique β-position [3 + 2]-cycloaddition between γ-deconjugated butenolides and spiro-epoxyoxindoles catalyzed by Sc(OTf)<sub>3</sub> has been disclosed. A variety of unexpected [3 + 2]-cycloaddition adducts of spiro-oxindoles fused with bicyclic γ-lactones and three consecutive stereocenters have been successfully constructed in good yields (up to 88%) with excellent diastereoselectivities (>20:1) in one single operation under mild conditions, which is difficult to achieve by traditional strategies.
Authors
- Guo Cheng (ORCID: https://orcid.org/0009-0002-2696-4740)
- Zhenyu Yang (ORCID: https://orcid.org/0000-0003-1857-1779)
- Wensheng Li (ORCID: https://orcid.org/0000-0003-4160-9317)
- Qian-Mao Zhang
- Jing-Liang Yu
- Li‐Xin Wang
- Chun-Chun Tang
Institutions
- Chinese Academy of Sciences (CN)
- Chengdu Organic Chemicals (China) (CN)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-03-18
- DOI
- https://doi.org/10.1021/acs.joc.4c02324
- Citations
- 1
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Key Research and Development Program of China