Date of Award

Spring 2015

Document Type

Thesis

Terms of Use

© 2015 Julia S. Murphy. All rights reserved. This work is freely available courtesy of the author. It may only be used for non-commercial, educational, and research purposes. For all other uses, including reproduction and distribution, please contact the copyright holder.

Degree Name

Bachelor of Arts

Department

Chemistry & Biochemistry Department

First Advisor

Robert S. Paley

Abstract

For many years, the Paley laboratory has developed the use of planar chiral η⁴ iron(O) tricarbonyl complexes for use in directing the central chirality of adjacent centers. This work examines the use of dienes functionalized at C2 with a chiral auxiliary. The functionalization of a stereocontrolled [6,6]-azaspirocycle was taken on to great success. This sequence involved a 2-sulfinyl diene complex. The keystone Grignard addition to the cyclic imine was accomplished to afford a single diastereomer. Ring closing metathesis was used to form the final ring of the azaspirocycle framework. Two more sequences were attempted to form azaspirocycle centers. The first was an attempt to employ an intramolecular Mannich. In this sequence, the cyclic imine and an enol would form in situ in order to avoid isolating the imine species which has been known to decompose. The final attempt at azaspirocycle formation was an attempt to directly replace a tertiary alcohol with an amine, again in an attempt to avoid the imine species. An alternative project working to use an alternative chiral auxiliary, an oxazolidinone, was also developed. The 2-oxazolidinyl diene complex was successfully complexed and new developments in this sequence included the development of a stannyicupration directed by a propargylic acetal in order to have an aldehyde adjacent to the diene complex.

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