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  • Title: Chemoselective oxygen-centered radical cyclizations onto silyl enol ethers.
    Author: Zlotorzynska M, Zhai H, Sammis GM.
    Journal: Org Lett; 2008 Nov 06; 10(21):5083-6. PubMed ID: 18855396.
    Abstract:
    A new oxygen-centered radical cyclization onto silyl enol ethers has been developed and utilized for the synthesis of versatile siloxy-substituted tetrahydrofurans. The reactions display excellent chemoselectivity for cyclization onto the electron-rich silyl enol ether when competing terminal alkene cyclization, 1,5-hydrogen abstraction, and beta-fragmentation pathways are present. The increased chemoselectivity also allows for the synthesis of tetrahydropyrans, a challenging substrate class to access using oxygen-centered radical alkene cyclizations due to competing 1,5-hydrogen abstractions.
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