|Title||Chemoselective Oxygen-Centered Radical Cyclizations onto Silyl Enol Ethers|
|Publication Type||Journal Article|
|Year of Publication||2008|
|Authors||Zlotorzynska, M, Zhai, H, Sammis, GM|
|Type of Article||Article|
|Keywords||4-PENTEN-1-OXYL RADICALS, ALKOXY RADICALS, CHEMISTRY, GENERATION, ORGANIC-SYNTHESIS, REDUCING AGENT, RING-CLOSURE REACTIONS, SELECTIVITY, STEREOSELECTIVE-SYNTHESIS, TETRAHYDROFURANS|
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|