Hexafluoroisopropanol-Enabled Access to Spirocyclobutanes via Cyclopropylcarbinyl Cation Rearrangement
Accessing spirocyclobutanes via cyclopropylcarbinyl cation rearrangements remains challenging due to competing pathways. Herein, we report an HFIP-enabled, BF<sub>3</sub>-catalyzed rearrangement-cyclization of cyclopropylcarbinyl alcohols, delivering diverse spirocyclobutanes in up to 95% yield. Subsequent derivatizations highlight synthetic utility, while DFT studies reveal that HFIP reshapes the reaction energy landscape to enhance the reactivity and selectivity.
Authors
- Yao Lu (ORCID: https://orcid.org/0000-0001-6784-8303)
- Xi-Liang Liu
- Ping Tian
- Qing-Hua Li
- Bei-Hai Geng
- A-Hui Li
- Zhi-Feng Hao
Institutions
- Shanghai University of Traditional Chinese Medicine (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-03-02
- DOI
- https://doi.org/10.1021/acs.orglett.6c00248
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00