Investigation of a Highly Selective Asymmetric Synthesis Strategy for <i>cis</i>-2-Fluorocyclopropanecarboxylic Acid: The Key Component of Sitafloxacin
A high-precision asymmetric synthetic route for <i>cis</i>-2-fluorocyclopropanecarboxylic acid with excellent stereoselectivity and regioselectivity was developed from commercially available starting materials, namely, fluoromethylphenylsulfone and chiral glycidyl derivatives, on a 100 g scale at the start. Despite the high overall yield, the synthetic route is remarkable for its brevity. This strategy forms the basis for further production of sitafloxacin on an industrial scale and provides an affordable and high-quality product.
Authors
- Chao Tan (ORCID: https://orcid.org/0000-0002-8910-1689)
- Lin Dong (ORCID: https://orcid.org/0000-0002-8004-821X)
- Wen Ao (ORCID: https://orcid.org/0000-0001-9245-6475)
- Lingxi Zhang (ORCID: https://orcid.org/0000-0003-1305-5222)
- Dong Ding (ORCID: https://orcid.org/0000-0001-5176-2046)
- Jing Zheng (ORCID: https://orcid.org/0000-0002-8269-9809)
- Bing-Tong Li
- Yu Gao (ORCID: https://orcid.org/0009-0000-5393-6310)
Institutions
- Sichuan University (CN)
- Buchang Pharma (China) (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-11-27
- DOI
- https://doi.org/10.1021/acs.joc.4c02299
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.21
Funders
- Higher Education Discipline Innovation Project
- Fundamental Research Funds for the Central Universities