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Date of Award

Spring 2023

Document Type

Masters Thesis

Department or Program Affiliation

WWU Chemistry Department

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

O'Neil, Gregory (Gregory W.)

Second Advisor

Antos, John M.

Third Advisor

Scheuermann, Margaret Louise

Abstract

A series of allylic sulfones were synthesized containing a stereodirecting group and chelating element and subjected to samarium diiodide reductions in the presence of a proton donor. The resulting products could be obtained with high regioselectivity (no less than 95:5) and high diastereoselectivity (>10:1) that correlated with the size of the stereodirecting group. A mechanism is proposed that includes loss of the sulfone and formation of a chelated organosamarium intermediate followed by intramolecular protonation by a samarium-bound proton source. In this way, both the regioselectivity and absolute stereochemistry of the resulting products are explained.

Type

Text

Keywords

Samarium Diiodide, Diastereoselective, Regioselective, Sulfone, Aldehyde, Epoxide

Publisher

Western Washington University

OCLC Number

1381363423

Subject – LCSH

Sulfones; Samarium; Reduction (Chemistry); Chemistry, Organic

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 document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.

Rights Statement

http://rightsstatements.org/vocab/NKC/1.0/

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