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

Brisa Hurlocker, Matthew R. Miner and K. A. Woerpel*

*Department of Chemistry, New York University, New York, New York 10003, United States, Email: kwoerpelnyu.edu

B. Hurlocker, M. R. Miner, K. A. Woerpel, Org. Lett., 2014, 16, 4280-4283.

DOI: 10.1021/ol5020015  (free Supporting Information)


Abstract

A cobalt-catalyzed peroxidation of silyl enol ethers with molecular oxygen and triethylsilane provides silyl monoperoxyketals in good yield. These compounds serve as precursors to peroxycarbenium ions, which undergo annulations to provide 1,2-dioxolanes.

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Key Words

peroxides, O-heterocycles, oxygen


ID: J54-Y2014