Class of 2014

Many of the molecules essential for life are inherently dissymmetric. Enantioselective organocatalysis—the synthesis of enantioenriched products from achiral or racemic starting materials through the use of small organic catalysts—can provide inexpensive, environmentally friendly access to such compounds. This thesis describes efforts toward the development of new organocatalytic methodologies for the enantioselective synthesis of a particularly important class of molecules, highly functionalized dihydrofuranoids, through the catalytic, asymmetric “interrupted” Feist-Bénary (IFB) reaction. Our initial work focused on the IFB reaction of α-halopropiophenones with dimedone in the presence of bis(cinchona alkaloid)pyrimidine catalysts. Though this reaction proceeded with only moderate enantioselectivity (up to 67 % ee) and disappointing yields (29-36%), it demonstrated that substituted bis(cinchona alkaloid)pyrimidines can induce chirality in the reactions of electrophiles bearing only one hydrogen bond acceptor