Chemodivergent and Enantioselective Synthesis of Spirobi[dihydrophenalene] Structures
The development and enantioselective synthesis of two types of <i>C</i><sub>2</sub>-symmetric spirobi[dihydrophenalene] structures is reported. The reaction proceeds via rhodium-catalyzed 2-fold asymmetric conjugate arylation of dienones followed by BF<sub>3</sub>·OEt<sub>2</sub>-promoted spirocyclization to give the enantiopure spiro products. Additive-dependent chemodivergent synthesis of 3,3'-diarylated 2,2',3,3'-tetrahydro-1,1'-spirobi[phenalene]-9,9'-diols (3,3'-Ar<sub>2</sub>-SPHENOLs) and the corresponding spiro diary ethers from the same intermediate is achieved. The structural properties of 3,3'-Ph<sub>2</sub>-SPHENOL are analyzed, and its application in asymmetric catalysis has been preliminarily demonstrated.
Authors
- Xiaowei Dou (ORCID: https://orcid.org/0000-0002-0748-1279)
- Peng Chuan-yong
- Fei Xue (ORCID: https://orcid.org/0000-0002-9257-5076)
- Changhui Wu (ORCID: https://orcid.org/0000-0002-3325-562X)
- Chenhong Wang (ORCID: https://orcid.org/0000-0003-4272-435X)
- Junhao Xing
Institutions
- China Pharmaceutical University (CN)
- Nanjing Forestry University (CN)
- Nanjing University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-01-10
- DOI
- https://doi.org/10.1021/acs.orglett.4c04612
- Citations
- 9
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 8.42
Funders
- Natural Science Foundation of Jiangsu Province
- Fundamental Research Funds for the Central Universities