The asymmetric induction in radical reactions by a chiral complexing agent was investigated. Enantiotopic differentiation is feasible due to complexation via hydrogen bonding to a prochiral substrate, which can be converted stereoselectively. Thus, enantioselective radical cyclisation reactions of heteroatom-substituted quinolone derivatives and addition reactions to oxindole derivatives were accomplished with high enantioselectivities (up to 99% ee). Furthermore, binding properties in complexation were analysed resulting in the determination of binding constants. A non-linear dependence of the enantiomeric excess was revealed. In addition, studies towards a template-induced conformational flip of non-cyclic amides and a potential activation via hydrogen bonding were conducted.
«
The asymmetric induction in radical reactions by a chiral complexing agent was investigated. Enantiotopic differentiation is feasible due to complexation via hydrogen bonding to a prochiral substrate, which can be converted stereoselectively. Thus, enantioselective radical cyclisation reactions of heteroatom-substituted quinolone derivatives and addition reactions to oxindole derivatives were accomplished with high enantioselectivities (up to 99% ee). Furthermore, binding properties in complexat...
»