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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.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:organic methods, organic synthesis, catalysis
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Not set
Research Advisor(s):
  • Stoltz, Brian M.
Thesis Committee:
  • Reisman, Sarah E. (chair)
  • Hsieh-Wilson, Linda C.
  • Nelson, Hosea M.
  • Stoltz, Brian M.
Defense Date:10 June 2025
Funders:
Funding AgencyGrant Number
National Institute of General Medical SciencesR01GM080269
National Institute of General Medical SciencesR35GM145239
National Institute of General Medical SciencesR35GM118191
Record Number:CaltechTHESIS:06262025-215200160
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:06262025-215200160
DOI:10.7907/hqt6-e038
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.3c04834DOIPortions of article adapted for Chapter 1.
https://doi.org/10.1021/acs.orglett.4c02551DOIPortions of article adapted for Chapter 2.
https://doi.org/10.1002/anie.202502583DOIPortions of article adapted for Chapter 3.
ORCID:
AuthorORCID
Barbor, Jay Park0000-0003-2787-4923
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:17492
Collection:CaltechTHESIS
Deposited By: Jay Barbor
Deposited On:09 Jul 2025 19:54
Last Modified:09 Jul 2025 19:54

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