The Studies On The Synthesis Of The Neolignan Cochinchin And The Influence Of Electronic Effects Of Stilbene Substrate On Catalytic Reaction

This paper aims as the studies on the synthesis of 1,4-benzodioxane neolignan Cochinchin and the influence of electronic effects of Stilbene substrate on catalytic reaction , mainly consists of following part:Chapter 1: Various neolignans, including their recently synthetic methods and classification, are reviewed in this chapter.Chapter 2: The latest application of powerful catalysts for asymmetric epoxidation of unfunctionalized olefins are reviewed.Chapter 3: We design two route for the synthesis of the 1, 4-benzodioxane neolignan Cochinchin: oxidative coupling and acid catalytic cyclization. The synthesis of Cochinchin was not accomplished from compound 5 and compound 19 via a strategy of biomimetic oxidative coupling, but to afford 7, 8 - trans-7', 8'-trans-resveratrol dehydrodimer tetramethyl ether 20. So the route that Merlini introduced to synsthesize this kind of 1, 4-benzodioxane neolignan does not suit the synthesis of Cochinchin. On the contrary, the second route we designed for the synthesis of the 1, 4-benzodioxane neolignan Cochinchin is reasonable.Chapter 4: Because electronic effects have seldom been reported to control enantioselectivity even though the electronic properties of both the catalyst and substrate can have profound effects in catalytic processes, and in the limited number of studies of electronic effects, our interest in this field has prompted us to design and synthesize a series of trans-olefins ( Stilbene:18, 34, 37, 41, 42, 47, 52, 57, 58, 60) to study the electronic effects of substrate in catalytic reaction. In the system of asymmetric epoxidation catalyzed by chiral ketone, the reactional conditions of trans-olefins have influenced by the kinds of substituents (electron-withdrawing groups or electron-donating groups) and their positions. We also propose an analysis to account for the electronic effects of those substituents.Chapter 5: Experimental section.Chapter 6: We synthesize sixties compounds, in which more than twenty are new compounds. 1H NMR, 13C NMR, IR, HRMS and element analysis were used to firm the structures of these compounds and the targets were successfully synthesized in this paper.