Three-Component 1,3-Difunctionalization of Carbonyl Ylides with Water and Azadienes for the Synthesis of Dihydroisobenzofurans
Multicomponent reactions are an efficient and widely employed synthetic strategy, known for their capability to rapidly and effectively construct complex molecular architectures from multiple starting materials. This work presents a chemo- and diastereoselective three-component reaction for the 1,3-difunctionalization of transient carbonyl ylides with H<sub>2</sub>O and azadienes, facilitated by the synergistic catalysis of Rh<sub>2</sub>(OAc)<sub>4</sub> and phosphoric acid. This strategy provides an efficient protocol for the synthesis of highly functionalized dihydroisobenzofurans in high yields (up to 94%) and good diastereoselectivities (up to 91:9 dr). Additionally, subsequent transformations with nucleophiles enable the synthesis of structurally diverse compounds with enhanced diastereoselectivities (dr >95:5).
Authors
- Jie Ren (ORCID: https://orcid.org/0000-0002-2505-6030)
- Wenhao Hu (ORCID: https://orcid.org/0000-0003-1511-2614)
- Yaxin Li (ORCID: https://orcid.org/0000-0003-0249-7148)
- Shijing Wu (ORCID: https://orcid.org/0000-0002-9438-5487)
- Haiqing Wang (ORCID: https://orcid.org/0000-0002-6805-2283)
- Yunzhe Wang
- Xiang Fu (ORCID: https://orcid.org/0009-0003-1691-6283)
Institutions
- Sun Yat-sen University (CN)
- Drug Discovery Laboratory (Norway) (NO)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-27
- DOI
- https://doi.org/10.1021/acs.orglett.5c00572
- Citations
- 1
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- China Postdoctoral Science Foundation
- Special Project for Research and Development in Key areas of Guangdong Province