Publication Date

2018

Document Type

Dissertation/Thesis

First Advisor

Gilbert, Thomas M.||Adler, Marc Jordan, 1981-

Degree Name

Ph.D. (Doctor of Philosophy)

Legacy Department

Department of Chemistry and Biochemistry

LCSH

Organic chemistry; Chemistry

Abstract

In this work 1-Hydrosilatrane has shown great potential to be a commodity reducing reagent in organic synthesis. Initially, 1-hydrosilatrane was investigated as a reducing reagent in the transformation of aldehydes to corresponding alcohols. Although initial investigations did not confirm previously published work, after addition of a Lewis base activator 1-hydrosilatrane demonstrated speedy reductions of many functionalized aryl aldehydes to alcohols with good yields. Next, 1- hydrosilatrane was used in a direct reductive amination reaction between primary amines and aldehydes/ketones. Reaction proceeded in the presence of a Bronsted acid, and resulted in excellent yields. This reaction was then expanded to chiral Bronsted acids and demonstrated the potential of 1-hydrosilatrane as a reagent in chiral reactions with enantiomeric excess of up to 84%. This work demonstrates versatility of 1-hydrosilatrane and presents it as a must have reagent in every organic chemistry lab.

Comments

Advisors: Thomas M. Gilbert; Marc J. Adler.||Committee members: Timothy Hagen; Douglas Klumpp; Carol Thompson.||Includes illustrations.||Includes bibliographical references.

Extent

179 pages

Language

eng

Publisher

Northern Illinois University

Rights Statement

In Copyright

Rights Statement 2

NIU theses are protected by copyright. They may be viewed from Huskie Commons for any purpose, but reproduction or distribution in any format is prohibited without the written permission of the authors.

Media Type

Text

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