Singlet Oxygen for Use in Organic Synthesis

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The central topic of this project is the investigation of singlet oxygen chemistry and its application for the synthesis of polyoxyfunctionalized products. Combining singlet oxygen reactions and subsequent oxygen transfer reactions leads to highly functionalized products with stereochemical information which slem from the initial photooxygenation step. There are four major areas which should be investigated: A) synthesis with 1O2, B) secondary oxygen transfer, C) 1O2 tandem reactions, D) 1O2endoperoxide transformation. In part A, stereoselective synthetic applications of singlet oxygen reactions are to be investigated with emphasis on stereocontrol by hydrogen-bonding and by organocatalytic methods; in part B, products (allylic hydroperoxides and endoperoxides, respectively) that are generated by singlet oxygen reactions are investigated with respect to secondary reductive or oxygen-transfer steps; in part C, tandem processes (1O2/1O2) are developed and investigated in order to find efficient ways to polyoxyfunctionalizations of organic substrates; in part D, possible enantioselective transformations of endoperoxides will be investigated.