Highly Enantioselective Palladium-Catalyzed Allylic Alkylation Reactions of Carbocyclic Enaminones and Acyclic Substrates

Author: Duquette, Douglas Charles

Year: 2017

Degree: Dissertation (Ph.D.)

Advisor: Stoltz, Brian M.

Committee Members: Stoltz, Brian M.; Reisman, Sarah E.; Agapie, Theodor; Gray, Harry B.

Option: Chemistry

DOI: 10.7907/Z9S46Q0P

Abstract

This report details the studies of the palladium-catalyzed asymmetric allylic alkylation reactions of carbocyclic substrates, specifically of vinylogous amides and enaminones, resulting in the discovery of a new substrate class (enaminones) with the highest enantioselectivies observed for this catalytic system to date. Moreover, conditions were discovered and developed for the asymmetric allylic alkylation of acyclic substrates by the selective formation of fully substituted enolates and application of a novel C2-symmetric Pd ligand.

Files

• DCD_Thesis_Final_05312017.pdf (application/pdf)