16765-45-0Relevant articles and documents
Ring-Contraction Reaction of Substituted Tetrahydropyrans via Dehydrogenative Dual Functionalization by Nitrite-Catalyzed Double Activation of Bromine
Watanabe, Kazuhiro,Hamada, Tsukasa,Moriyama, Katsuhiko
, p. 5803 - 5807 (2018/09/21)
A nitrite-catalyzed ring contraction reaction of substituted tetrahydrofurans by oxidation of bromide under aerobic conditions as a dehydrogenative dual functionalization was developed to provide 2-acyltetrahydrofurans in good yields. On the other hand, the oxidation reaction of 1-substituted isochromans occurred via the bromohydroxylation to give 1-(dibromoalkyl)-1-hydroxyisochromans in high yields.
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.
New method for the synthesis of α-substituted tetrahydrofuran -2-methanols through diastereoselective addition of THF to aldehydes mediated by Et3B in the presence of air
Yoshimitsu, Takehiko,Tsunoda, Maki,Nagaoka, Hiroto
, p. 1745 - 1746 (2007/10/03)
The tetrahydrofuranyl radical, generated from THF with Et3B in the presence of air, was found to react with aldehydes threo-selectively to afford α-substituted tetrahydrofuran-2-methanols, the common structural motifs of biologically active ace