A Synthetic Method for Spirocyclobutanes via Ring Expansion of Donor–Acceptor Spirocyclopropanes with Stabilized Sulfonium Ylides
A sulfonium ylide-mediated ring expansion of donor-acceptor spirocyclopropanes has been developed to provide access to spirocyclobutanes. Spirocyclopropanes derived from 1,3-indandione undergo efficient ring expansion with stabilized sulfonium ylides, affording the corresponding spirocyclobutanes as single isomers in high yield. Given that spirocyclic frameworks, with their rigid three-dimensional architecture, play a key role in drug discovery, spirocyclobutanes represent particularly promising core structures. This synthetic method is expected to make a significant contribution to pharmaceutical development.
Authors
- Hisanori Nambu (ORCID: https://orcid.org/0000-0002-5186-8868)
- Kōta Yoshioka (ORCID: https://orcid.org/0000-0002-2937-3842)
- Keisuke Tomohara (ORCID: https://orcid.org/0000-0003-2305-5963)
- Rika Sakai (ORCID: https://orcid.org/0000-0002-5832-5268)
- Hikaru Fujii
Institutions
- Kyoto Pharmaceutical University (JP)
- State Key Laboratory of Synthetic Chemistry (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-05-10
- DOI
- https://doi.org/10.1021/acs.joc.6c00210
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00