Phosphine-Catalyzed [4 + 1] Annulation of β’-Acetoxy Allenoate with α-Alkylidene Succinimides: Access to Functionalized Spirosuccinimide Derivatives
A phosphine-catalyzed [4 + 1] annulation of β'-acetoxy allenoate with α-alkylidene succinimides is described. This method demonstrates the nucleophilic dialkylation and cyclization of α-alkylidene succinimides, resulting in the formation of functionalized spirosuccinimide derivatives. The reaction exhibits a wide substrate scope and yields ranging from moderate to excellent under the optimized conditions. In addition, the biological evaluation indicates that the cycloadduct <b>3u</b> presents satisfied inhibitory activities for three human cancer cell lines (HCT116, A549, and HepG2).
Authors
- Chunjie Ni (ORCID: https://orcid.org/0000-0003-1479-5484)
- Xiaojuan Xu (ORCID: https://orcid.org/0000-0003-1869-930X)
- Chen Chen (ORCID: https://orcid.org/0000-0002-5388-9611)
- Fan Yu (ORCID: https://orcid.org/0000-0003-0866-9270)
- Yining Zhao (ORCID: https://orcid.org/0000-0002-7851-0890)
- Zhanhang Liang
Institutions
- Nanjing Tech University (CN)
- Tianjin Normal University (CN)
- Yancheng Teachers University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-10-31
- DOI
- https://doi.org/10.1021/acs.joc.4c02014
- Citations
- 3
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Jiangsu Province
- Yancheng Science and Technology Bureau
- Natural Science Research of Jiangsu Higher Education Institutions of China