Synthesis Of Chiral Brφnsted Acid And Application To Photochemical Reaction

Visible light has unique advantages which are inexpensive, environmentfriendly, easily renewable source of clean energy. With the emergence ofvisible-light catalyst Ru(bpy)32+, more and more organic reation can harness visiblefor chemical transformation. Especially, utilizing visible light to induceMannich-type reactions successfully functionalization of sp3C–H bond adjacent tonitrogen. However, the product turned out to be racemization.On the other hand, a large number of valuable organic molecules, such asmedicine, in our daily life are chiral and we can’t live without them. Meanwhile, theexisting chiral synthesis is nonenvironmentally friendly, inefficient, high energycompustion as well as limited application scope. This paper is aimed to solvingthese problems using visible light to generate chiral compounds.According to the literature research, we decided to use chiral brφnsted acidco-catalysis with visible light photoredox to give chiral product. After studied on themechanism, it was possible that the chiral brφnsted acid will co-working with visiblelight catalyst to induce chiral derivatives of1,2,3,4-tetrahydroisoquinoline.The first work is preparing substrates, then tested the conditions for highperformance liquid of products. Next we used achiral cyclic phosphoric acid diesterto find optimal condition. It showed using the CH3OH as solvent, in the roomtemperature under the LED light source as the basic condition.Finally, we synthesized about ten kinds of chiral brφnsted acid according to theclassical methods and then test their catalytic efficiency. Their effect to thereactions was been researched. We analysed the data objectively, and studied on thepossible reasons of such result.All of the products were characterized by NMR, IR and HRMS analysis.