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Date Permissions Signed

6-4-2018

Date of Award

Spring 2018

Document Type

Masters Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

O'Neil, Gregory (Gregory W.)

Second Advisor

Vyvyan, James R.

Third Advisor

Gilbertson, John D.

Abstract

Herein, we report a regio- and diastereoselective samarium mediated allylic benzoate reduction. The reaction can achieve high yields, regioselectivity, and diastereoselectivity, however there appear to be many factors influencing the outcome: proton sources, alkene geometry, chelating group length, relative stereocenter positioning, and stereocenter identity. These substrate parameters were looked at in-depth which ultimately led to several conclusions about optimized substrates. For instance, experiments indicate that the reaction proceeds through a bicyclic organosamarium species followed by intramolecular protonation from samarium bound water.

Type

Text

Keywords

Samarium diiodide, regioselective, diastereoselective, organosamarium, stereoselective synthesis

DOI

https://doi.org/10.25710/stbr-3d39

Publisher

Western Washington University

OCLC Number

1039724345

Subject – LCSH

Samarium; Iodides; Benzoates; Reduction (Chemistry); Asymmetric synthesis

Format

application/pdf

Genre/Form

masters theses

Language

English

Rights

Copying of this document 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.

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