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Date Permissions Signed

5-29-2015

Date of Award

Spring 2015

Document Type

Masters Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Vyvyan, James R.

Second Advisor

Antos, John M.

Third Advisor

Emory, Steven R.

Abstract

Gold catalysis has emerged over the past decade as an important methodology in the construction of organic molecules. Cationic gold complexes are robust, versatile, selective and efficient catalysts that can be used to enhance the electrophilicity of C-C unsaturated bonds. A current area of investigation is the use of gold to activate allylic alcohol/ether moieties for intramolecular SN2’ nucleophilic attack to form oxygen heterocycles. We have discovered that sterically bulky, electron-withdrawing oxygen leaving groups drastically improved reaction efficiency, and bulky leaving groups in combination with substrate substituents enhanced diastereomeric ratios in the oxygen heterocycle products. These reactions proceeded smoothly in the presence of many functional groups to consistently afford high diastereoselectivity. This methodology was attempted in the synthesis complex spirocyclic ether structures, and used in progress towards total synthesis of the natural product (±)-centrolobine.

Type

Text

Publisher

Western Washington University

OCLC Number

910675332

Digital Format

application/pdf

Genre/Form

Academic theses

Language

English

Rights

Copying of this thesis in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this thesis for commercial purposes, or for financial gain, shall not be allowed without the author's written permission.

Included in

Chemistry Commons

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