2012 Theses Doctoral

Enantioselective (Formal) Aza-Diels-Alder Reactions with Danishefsky's Diene and Non-Danishefsky Type Dienes

Lee, Sharon Kim

Highly functionalized piperidines represent an important class of heterocycles that are found in natural products and medicinally active agents. As a direct result, efforts to develop enantioselective diene-imine (aza-Diels-Alder) reactions to efficiently access these substructures have increased. We have developed highly enantioselective silicon Lewis acid mediated formal aza-Diels-Alder reactions with Danishefsky's diene and non-Danishefsky's dienes to generate these biologically important heterocycles. To further prove the power of this method to access complex piperidine structures, we have accomplished the efficient enantioselective synthesis of the drug target casopitant.