The vast majority of theses in this collection are open access and freely available. There are a small number of theses that have access restricted to the WWU campus. For off-campus access to a thesis labeled "Campus Only Access," please log in here with your WWU universal ID, or talk to your librarian about requesting the restricted thesis through interlibrary loan.
Date of Award
Department or Program Affiliation
WWU Chemistry Department
Master of Science (MS)
O'Neil, Gregory (Gregory W.)
Antos, John M.
Scheuermann, Margaret Louise
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.
Samarium Diiodide, Diastereoselective, Regioselective, Sulfone, Aldehyde, Epoxide
Western Washington University
Subject – LCSH
Sulfones; Samarium; Reduction (Chemistry); Chemistry, Organic
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.
Schwans, Cody, "Regio- and Diastereoselective Samarium-Mediated Allylic Sulfone Reductions" (2023). WWU Graduate School Collection. 1204.