CaltechTHESIS
  A Caltech Library Service

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

Citation

Duquette, Douglas Charles (2017) Highly Enantioselective Palladium-Catalyzed Allylic Alkylation Reactions of Carbocyclic Enaminones and Acyclic Substrates. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/Z9S46Q0P. http://resolver.caltech.edu/CaltechTHESIS:05042017-104254217

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.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:catalysis, palladium, asymmetric catalysis, enaminone, vinylogous amide, allylic alkylation
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Stoltz, Brian M.
Thesis Committee:
  • Stoltz, Brian M.
  • Reisman, Sarah E. (chair)
  • Agapie, Theodor
  • Gray, Harry B.
Defense Date:19 December 2016
Funders:
Funding AgencyGrant Number
National Science FoundationDGE- 1144469
Record Number:CaltechTHESIS:05042017-104254217
Persistent URL:http://resolver.caltech.edu/CaltechTHESIS:05042017-104254217
DOI:10.7907/Z9S46Q0P
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/adsc.201500253DOIArticle adapted for Appendix 4.
http://dx.doi.org/10.1021/acs.orglett.5b01292DOIArticle adapted for Appendix 5.
http://dx.doi.org/10.1002/chem.201300030DOIArticle adapted for Chapter 1.
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:10155
Collection:CaltechTHESIS
Deposited By: Douglas Duquette
Deposited On:02 Jun 2017 19:29
Last Modified:23 Jan 2019 18:33

Thesis Files

[img]
Preview
PDF - Final Version
See Usage Policy.

29Mb

Repository Staff Only: item control page