UC Davis

This dissertation describes four synthetic organic chemistry projects and two computational organic chemistry efforts centered on the Castagnoli-Cushman reaction (CCR) of imines with anhydrides and their derivatives. Chapter one includes a literature review and detailed background on the current state of the CCR, including mechanistic hypotheses and recent catalytic examples. Chapter two details the development of conjugate addition reactions of imines with cyclic enolizable anhydrides to afford β-enaminoketone products. Chapter three describes efforts toward an acid-catalyzed Mukaiyama-type CCR reaction of 2,5-bis(trimethylsilyloxy) furan, including a stereochemical proof by computational NMR. Chapter four describes progress toward the synthesis of the elusive bis-?-lactam natural product bisavenanthramide B-1 by way of the Mukaiyama CCR. Finally, chapter five discusses the mechanistic investigation of the multicomponent variants of the CCR, leading to a new mechanistic proposal for reactions of these type.