Au(PPh<sub>3</sub>)Cl/AgOTf/TsOH-Catalyzed Cascade Reaction between 1-(2-Hydroxyphenyl)-propargyl Alcohols and β-Oxoketones (Amides, Acid): Diastereoselective Construction of <i>cis</i>-3a,8a-Dihydrofuro[2,3-<i>b</i>]benzofuran Framework
In the Au(PPh<sub>3</sub>)Cl/AgOTf/TsOH/MeCN/N<sub>2</sub>/25 °C system, diastereoselective synthesis of <i>cis</i>-3a,8a-dihydrofuro[2,3-<i>b</i>]benzofuran derivatives with a substituent at the 8a-position has been achieved by using 1-(2-hydroxyphenyl)-3-arylprop-2-yn-1-ols and β-oxoketones (amides, acid) as starting materials. The studies revealed that the acidity of methylene in substrates plays a key role in the differential reactions. A stronger acidity of the methylene is favorable in the desired conversion. The unique role of TsOH as an additive acid in the synthesis strategy has been rationalized. 2-Oxo-phosphonate, 2-oxo-sulfonate, and 3-oxobutanoate are suitable for the conversion.
Authors
- Yangyi Zhang (ORCID: https://orcid.org/0000-0002-5465-6334)
- Guisheng Deng (ORCID: https://orcid.org/0000-0002-6132-5648)
Institutions
- Hunan Normal University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-11-20
- DOI
- https://doi.org/10.1021/acs.joc.4c02430
- Citations
- 4
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.00