Development of a kinetic resolution based on mechanistic insight into the tert-butyl hydroperoxide-mediated wacker oxidation

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Title Development of a kinetic resolution based on mechanistic insight into the tert-butyl hydroperoxide-mediated wacker oxidation
Publication Type thesis
School or College College of Science
Department Chemistry
Author Steffens, Laura Daly
Date 2012-05
Description The Wacker oxidation is a well-known and widely utilized reaction in synthetic organic chemistry for the transformation of terminal alkenes to methyl ketones using catalytic palladium. The recently described tert-butyl hydroperoxide (THBP)-mediated Wacker oxidation using the quinoline-oxazoline (Quinox) ligand has proven to be a ligand-controlled transformation with broad tolerance for a wide range of classical, challenging substrates with varying functionality. The development of an asymmetric variant of this reaction is necessary to broaden its utility. A kinetic resolution applied to Wacker transformations of acyclic substrates has not yet been described in the literature, and the utility of the resultant enantioenriched starting materials and products make it a compelling goal. Described herein is the development of a kinetic resolution for the TBHPmediated Wacker oxidation of terminal alkene substrates. A detailed mechanistic study of the symmetric transformation, as well as prior work performed by previous group members, provided the foundation for the approach to ligand modulation, succeeded by solvent, substrate, and counter ion optimization. Though optimal results have not yet been achieved, significant insight into each of these reaction parameters has been garnered for further study and progression of this methodology.
Type Text
Publisher University of Utah
Subject Kinetic resolution; Wacker oxidation; Palladium; Quinox; Resolution; Wacker
Subject LCSH Oxidation
Dissertation Institution University of Utah
Dissertation Name Master of Science
Language eng
Rights Management Copyright © Laura Daly Steffens 2012
Format application/pdf
Format Medium application/pdf
Format Extent 9,950,353 bytes
Identifier us-etd3,84237
ARK ark:/87278/s69s25rx
Setname ir_etd
ID 194552
Reference URL https://collections.lib.utah.edu/ark:/87278/s69s25rx
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