On-DNA Three-Component Cycloaddition of Diazo Compounds, Nitrosoarenes, and Alkenes: Syntheses of Isoxazolidines for DNA-Encoded Chemical Libraries
A DNA-compatible three-component reaction is disclosed for the synthesis of on-DNA polysubstituted isoxazolidines that serve as privileged core scaffolds in numerous natural products and bioactive molecules. This one-pot approach involves the 1,3-dipolar cycloaddition of DNA-tagged styrenes with diazo compounds and nitrosoarenes in an aqueous solution of KOAc. The reaction demonstrates excellent functional group compatibility, providing a conventional protocol for the construction of a DNA-labeled isoxazolidine library.
Authors
- Xiang Fu (ORCID: https://orcid.org/0009-0002-9671-515X)
- Jie Ren (ORCID: https://orcid.org/0000-0002-2505-6030)
- Zhenghui Kang (ORCID: https://orcid.org/0000-0002-7489-1200)
- Wenhao Hu (ORCID: https://orcid.org/0000-0003-1511-2614)
- Yaxin Li (ORCID: https://orcid.org/0000-0003-0249-7148)
- Mingjin He
- Zhiwei Wei (ORCID: https://orcid.org/0000-0002-1304-4243)
Institutions
- Sun Yat-sen University (CN)
- Yantai University (CN)
- Chinese Academy of Sciences (CN)
- Shanghai Institute of Materia Medica (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-25
- DOI
- https://doi.org/10.1021/acs.orglett.4c04011
- Citations
- 11
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 2.75
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Guangdong Province