1076691-80-9Relevant academic research and scientific papers
Chemoselective oxygen-centered radical cyclizations onto silyl enol ethers
Zlotorzynska, Maria,Zhai, Huimin,Sammis, Glenn M.
supporting information; experimental part, p. 5083 - 5086 (2009/05/31)
(Chemical Equation Presented) 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 β-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.
