C(sp<sup>3</sup>)–H Oxidation of Spiroguanidine-Containing Cyclopentanes
A C(sp<sup>3</sup>)-H oxidation reaction for spiroguanidine compounds with 5-membered rings was developed. The introduction of a cyclopentane-fused aminomethylpyridine as a directing group to the amide linkage of the cyclic guanidine moiety, using H<sub>2</sub>O<sub>2</sub>-urea in trifluoroethanol, enabled oxidation at the spiro β-position of the cyclopentane ring. This allowed selective introduction of a hydroxy group at the spiro β-position and was applicable to cyclopentane compounds with various substituents, including those challenging to functionalize with common oxidation methods.
Authors
- Sangita Karanjit (ORCID: https://orcid.org/0000-0003-0151-5893)
- Yûki Kimura (ORCID: https://orcid.org/0000-0002-5054-8483)
- Kosuke Namba (ORCID: https://orcid.org/0000-0003-1548-5656)
- Ryota Sato (ORCID: https://orcid.org/0009-0005-6940-9159)
Institutions
- Tokushima University (JP)
- The University of Osaka (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-26
- DOI
- https://doi.org/10.1021/acs.joc.5c00714
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- University of Tokushima
- Japan Society for the Promotion of Science