Utilization of Rationally Designed Small Molecule Chiral Selectors in Novel Enantioselective Processes
Snyder, Seth Elliot
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https://hdl.handle.net/2142/82349
Description
Title
Utilization of Rationally Designed Small Molecule Chiral Selectors in Novel Enantioselective Processes
Author(s)
Snyder, Seth Elliot
Issue Date
2003
Doctoral Committee Chair(s)
Pirkle, William H.
Department of Study
Chemical Engineering
Discipline
Chemical Engineering
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
In addition, phase transfer catalyzed biphasic kinetic resolutions of several racemic amides containing electron-deficient aromatic moieties are described. The method revolves around forming Meisenheimer adducts which are stabilized by quaternary ammonium salts in a nonpolar medium. When run in the presence of a chiral selector, one enantiomer is effectively shielded from reaction. The methodology is extended to enantioselective nucleophilic aromatic substitution, reactions known to proceed through the intermediacy of a Meisenheimer adduct.
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