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Chemoselective Oxygen-Centered Radical Cyclizations onto Silyl Enol Ethers

TitleChemoselective Oxygen-Centered Radical Cyclizations onto Silyl Enol Ethers
Publication TypeJournal Article
Year of Publication2008
AuthorsZlotorzynska, M, Zhai, H, Sammis, GM
JournalOrganic Letters
Volume10
Pagination5083-5086
Date PublishedNov
Type of ArticleArticle
ISBN Number1523-7060
Keywords4-PENTEN-1-OXYL RADICALS, ALKOXY RADICALS, CHEMISTRY, GENERATION, ORGANIC-SYNTHESIS, REDUCING AGENT, RING-CLOSURE REACTIONS, SELECTIVITY, STEREOSELECTIVE-SYNTHESIS, TETRAHYDROFURANS
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.
URL<Go to ISI>://000260534500094