Oxidative Cyclization of 1,5-Dienes with Hydrogen Peroxide Catalyzed by an Osmium(III) Complex: Synthesis of cis-Tetrahydrofurans
datasetposted on 07.03.2016, 19:21 by Hideki Sugimoto, Takayuki Kanetake, Kazuki Maeda, Shinobu Itoh
Datasets usually provide raw data for analysis. This raw data often comes in spreadsheet form, but can be any collection of data, on which analysis can be performed.
Stereoselective oxidative cyclization of 1,5-dienes with hydrogen peroxide catalyzed by [OsIII(OH)(H2O)(L–N4Me2)](PF6)2 (1: L–N4Me2 = N,N′-dimethyl-2,11-diaza-[3,3](2,6)pyridinophane) is explored. 1,5-Dienes involving geraniol derivatives are converted to the corresponding tetrahydrofurans in modest to high yields. The products exclusively have the cis-conformation with respect to the substituents at the 2- and 5-positions of the tetrahydrofuran ring. The products also have a syn-conformation with respect to the furan oxygen atom and the hydroxyl groups. Mechanistic studies including a direct reaction of the oxo-hydroxo-osmium(V) complex, 2, with a dihydroxylated geraniol derivative are performed.