Journal of the American Chemical Society· 2026Q1
Synthesis of Medium-Sized Cyclic Ethers via Endo -Selective Pd(0)/B(C6F5)3-Catalyzed Hydroalkoxylation of Enynols and Enynediols
- 1citations
- Q1SCImago
- 2026year
Short summary
A new Pd(0)/B(C6F5)3-catalyzed method synthesizes 6- to 8-membered cyclic ethers from enynols and enynediols with high endo-selectivity.
AI-generated from the title and abstract; the full text is not read.
Key points
- Developed a Pd(0)/B(C6F5)3-catalyzed hydroalkoxylation for medium-sized cyclic ether synthesis.
- Achieved high endo-selectivity in the formation of 6- to 8-membered oxacycles.
- Demonstrated utility via total synthesis of (±)-corypsoriol D and E.
- Elucidated a mechanism involving oxidative syn-outer-sphere proton transfer and reductive elimination.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract Medium-sized cyclic ethers are present in many natural products and therapeutic agents. Herein, we describe a mild catalytic method for the synthesis of 6- to 8-membered oxacycles by endo-selective hydroalkoxylation of enynols and enynediols. The utility of this method is demonstrated through the total synthesis of (±)-corypsoriol D and E. Experimental and computational mechanistic studies revealed an oxidative syn-outer-sphere proton transfer mechanism, followed by a rate-determining reductive elimination via nucleophilic attack of the alkoxide on the resulting Pd-π-allyl.
The authors' abstract, as published at the source. Journal of the American Chemical Society, 2026 · DOI ↗
Continue with a free account
Ask the paper: 3 free questions a day about this paper; save it, get its citation, new summaries every day for your field. Takeaways are Premium.
Continue free on the webSign in with Google or Apple; no card needed. You come back to this paper.
On your phone:
Field: Organic Chemistry
Organic ChemistryChemistry