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Date of Award

Spring 2025

Document Type

Masters Thesis

Department or Program Affiliation

Chemistry

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

O'Neil, Gregory (Gregory W.)

Second Advisor

Scheuermann, Margaret Louise

Third Advisor

Larsen, Michael B.

Abstract

The reduction of carbonyl compounds is a cornerstone of organic synthesis, essential for the construction of complex molecules. This report presents a novel methodology for carbonyl reductions, in which tetra-n-butylammonium triphenyldifluorosilicate (TBAT)-catalyzed hydrosilylation of β-hydroxyketones leads to the formation of dioxasilinane products. These cyclic, silicon-containing intermediates offer significant synthetic utility: an aqueous workup yields desilylated 1,3-diols, while treatment with nucleophilic reagents enables regioselective ring-opening to afford differentiated 1,3-diols. The selective protection of the secondary alcohol as a diphenylmethylsilyl (DPMS) ether is achieved when methyl lithium (MeLi) is used as the nucleophile. This efficient and improved method for the formation and isolation of dioxasilinanes from β-hydroxyketones is used in the formation of several diastereoselective dioxasilinane and DPMS ether products.

Type

Text

Keywords

organic synthesis, hydrosilylation, natural product synthesis, reaction optimization, TBAT

Publisher

Western Washington University

OCLC Number

1522125954

Subject – LCSH

Organic compounds--Synthesis; Hydrosilylation; Chemical reactions

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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