Synthesis of 1-Substituted Bicyclo[2.1.1]hexan-2-ones via a Sequential SmI<sub>2</sub>-Mediated Pinacol Coupling and Acid-Catalyzed Pinacol Rearrangement Reaction
A two-step procedure, combining a SmI<sub>2</sub>-mediated transannular pinacol coupling reaction with an acid-catalyzed pinacol rearrangement process, was employed to prepare a diverse range of 1-substituted bicyclo[2.1.1]hexan-5-ones from cyclobutanedione derivatives. To underscore the significance of these bicyclic ketones in drug synthesis, an sp<sup>3</sup>-rich analog of nitazoxanide, a well-known antiparasitic and antiviral agent, was synthesized.
Authors
- Woo‐Jin Yoo (ORCID: https://orcid.org/0000-0002-1207-9399)
- Yung‐Chi Lee
- Yi-Chen Chen (ORCID: https://orcid.org/0000-0001-8969-9927)
- Chunfu Wu
Institutions
- National Taiwan University (TW)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-22
- DOI
- https://doi.org/10.1021/acs.orglett.4c03541
- Citations
- 1
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- National Tsing Hua University
- National Taiwan Normal University
- National Taiwan University
- National Science and Technology Council
- Center for Emerging Material and Advanced Devices, National Taiwan University