Enantioselective Cascade Annulation of 1,2,3-Triazoles and Enals Enabled by Sequential Rhodium and Oxidative NHC Catalysis Involving Cleavage, Migration, and Cyclization
The in situ-generated pyrrolin-3-ones serve as novel and versatile synthons, being employed as intermediates for the efficient production of pyrrole-fused lactones with high yield and excellent enantioselectivity. Herein, we introduce emerging rhodium and oxidative N-heterocyclic carbene relay catalysis that enables a highly enantioselective cascade annulation between easily available 1,2,3-triazoles and enals. In this proof-of-concept study, the in situ-generated pyrrolin-3-ones engage α,β-unsaturated acylazolium intermediates generated from enals via oxidative N-heterocyclic carbene catalysis.
Authors
- Wenbin Wu (ORCID: https://orcid.org/0000-0002-0101-5621)
- Shenci Lu (ORCID: https://orcid.org/0000-0003-4357-455X)
- Zhifeng Tu
- Siew Yin Chan (ORCID: https://orcid.org/0000-0001-5326-2758)
- Hao An (ORCID: https://orcid.org/0000-0003-0919-2283)
- Fei Xue (ORCID: https://orcid.org/0000-0002-9257-5076)
- Xiaoyi Yu
- Yina Jiang
Institutions
- Agency for Science, Technology and Research (SG)
- Nanjing Forestry University (CN)
- Northwestern Polytechnical University (CN)
- Institute of Materials Research and Engineering (SG)
- Shaanxi University of Chinese Medicine (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-28
- DOI
- https://doi.org/10.1021/acs.orglett.5c00242
- Citations
- 3
- Primary Topic
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- National Natural Science Foundation of China
- Fundamental Research Funds for the Central Universities