Synthesis of Silyl Monoperoxyketals by Regioselective Cobalt-Catalyzed Peroxidation of Silyl Enol Ethers: Application to the Synthesis of 1,2-Dioxolanes

Synthesis of Silyl Monoperoxyketals by Regioselective Cobalt-Catalyzed Peroxidation of Silyl Enol Ethers: Application to the Synthesis of 1,2-Dioxolanes

The cobalt-catalyzed peroxidation of silyl enol ethers with molecular oxygen and triethylsilane provided silyl monoperoxyketals in 54%–96% yield. These compounds serve as precursors to peroxycarbenium ions, which undergo annulations to provide 1,2-dioxolanes.

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Veröffentlicht in:Organic letters 2014-08, Vol.16 (16), p.4280-4283
Hauptverfasser: Hurlocker, Brisa, Miner, Matthew R, Woerpel, K. A
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cobalt - chemistry
Combinatorial Chemistry Techniques
Cyclization
Dioxolanes - chemical synthesis
Dioxolanes - chemistry
Ethers - chemistry
Silanes - chemical synthesis
Silanes - chemistry
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Zusammenfassung:The cobalt-catalyzed peroxidation of silyl enol ethers with molecular oxygen and triethylsilane provided silyl monoperoxyketals in 54%–96% yield. These compounds serve as precursors to peroxycarbenium ions, which undergo annulations to provide 1,2-dioxolanes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5020015