Synergistic Cu(II)/Amine-Catalyzed Cyclization of Enynone: Assembly of Tetralone and Tetrahydronaphthylimine
An unprecedented synergistic copper- and amine-catalyzed cyclization of enynone is reported. This reaction features an efficient and straightforward construction of multisubstituted tetralone through an amine-assisted regioselective oxygen atom transfer process and stereoselective intramolecular Michael addition cyclization. Under dehydrative reaction conditions, the synthesis of tetrahydronaphthylimine derivatives with ketone group tolerance is achieved, which could be challenging via traditional methods. The utility of this reaction is demonstrated by further transformations of obtained molecules toward a variety of valuable multisubstituted naphthyl skeletons.
Authors
- Yun‐Hui Zhao (ORCID: https://orcid.org/0000-0002-9395-3876)
- Jiangan Liu
- Zhenqiang Tang
- Danling Tang (ORCID: https://orcid.org/0000-0002-4645-8688)
- Hu Zhou (ORCID: https://orcid.org/0000-0001-7006-4737)
- Shaotong Qiu
- Mei Luo (ORCID: https://orcid.org/0000-0003-4106-4476)
- Xiaofang Li (ORCID: https://orcid.org/0000-0003-0677-6689)
- Liu Xiong (ORCID: https://orcid.org/0000-0001-9916-116X)
- Zhicheng Yang (ORCID: https://orcid.org/0000-0001-5202-8433)
- Zhe Huang (ORCID: https://orcid.org/0000-0002-9201-9491)
- Y. Mao (ORCID: https://orcid.org/0000-0003-3184-7733)
- Z. X. Fan
Institutions
- Hunan University of Science and Technology (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-01-16
- DOI
- https://doi.org/10.1021/acs.orglett.4c04536
- Citations
- 4
- Primary Topic
- Traditional and Medicinal Uses of Annonaceae
- Type
- article
- Field-Weighted Citation Impact
- 4.45
Funders
- Natural Science Foundation of Hunan Province