Singlet Oxygen for Use in Organic Synthesis

本项目的中心课题是单线态氧化学的研究及其在合成多氧功能化产物中的应用。将单重态氧反应和随后的氧转移反应结合起来，可以得到具有立体化学信息的高度官能化的产物，这些信息从最初的光氧化步骤开始。有四个主要领域需要研究：A)1O2合成，B)二次氧转移，C)1O2串联反应，D)1O2内过氧物转化。在A部分，研究了单线态氧反应的立体选择性合成应用，重点是通过氢键和有机催化方法进行立体控制；在B部分，研究了单线态氧反应产生的产物(分别为烯丙基过氧化氢和内氧)的二次还原或氧转移步骤；在C部分，开发和研究了串联过程(1O2/1O2)，以寻找有机底物多氧官能化的有效方法；在D部分，将研究内氧化物可能的对映选择性转化。

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.