Stereoselective Route to 2,3,4,5-Tetraaryltetrahydrofurans via Efficient Cascade Synthesis of 2,3-Dihydrofurans with Four Different (Hetero)Aryl Substituents
Tf<sub>2</sub>NH-mediated regio- and diastereoselective skeletal metamorphosis of 1-alkynyl-2,3-diaryl-2-methoxycarbonylcyclopropyl ketones readily gave 2,3,4,5-tetraaryl-2,3-dihydrofurans. Controllable reduction and removal of the ester group then precisely afforded four types of the eight possible tetrahydrofuran (THF) diastereomers with four different (hetero)aryl substituents. Further, deuterium-labeling results revealed an unprecedented hydrogen transfer from the formyl C-H bond in <sup><i>t</i></sup>BuOK-promoted decarbonylation under <sup><i>t</i></sup>BuOH-free conditions.
Authors
- Sunewang Rixin Wang (ORCID: https://orcid.org/0000-0002-7099-2928)
- Haoran Wang (ORCID: https://orcid.org/0000-0001-8859-0348)
Institutions
- East China Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c00450
- Citations
- 1
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Shanghai Municipal Education Commission
- East China Normal University