Transition Metal-Catalyzed Methodologies for the Synthesis of Complex Amide Building Blocks

Citation

Barbor, Jay Park (2026) Transition Metal-Catalyzed Methodologies for the Synthesis of Complex Amide Building Blocks. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/hqt6-e038. https://resolver.caltech.edu/CaltechTHESIS:06262025-215200160

Abstract

Amides are ubiquitous functional groups that play a critical role in the composition and function of many biologically active molecules. Herein, this thesis presents three novel methodologies toward the construction of small molecules bearing amide functionality. In the first chapter, a convergent Ni-catalyzed N–N cross-coupling for the synthesis of hydrazides is described. This reaction constitutes the first example of a transition metal-catalyzed N–N bond forming reaction compatible with a wide array of aliphatic amine nucleophiles. In the second chapter, an enantioselective α-vinylation of γ-lactams is presented. In the third chapter, a novel, enantioselective spirocyclization of Pd-enolates intercepted under decarboxylative allylic alkylation conditions is disclosed. Finally, in the last appendices, we present a revised and expedient route toward the bis-THIQ natural product scaffold and describe the synthesis of some non-natural analogs.

Thesis Files