Abstract
Photooxygenation of titled furans followed by reduction gives unsaturated 4-oxoaldehydes quantitatively. Some derivatives cyclize under slightly acid conditions or by silica gel to unusual 5,6- dioxabicyclo[2.1.1]hexenes and/or 5H-furanones. Under appropriate basic conditions 4-oxocarboxylic acids or their ring-tautomers 5-hydroxyfuranones are chemoselectively obtained in almost quantitative yields. All the procedures are one-pot and occur stereoselectively. Due to the electron-poor substituents alternative non-photochemical oxidative methods fail or give not cleanly reaction mixtures.
Keywords: 4-oxo acids, 4-oxoaldehydes, base treatment, furan endoperoxides, reduction, singlet oxygen.
Graphical Abstract
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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