Design, Synthesis, and Applications of Chiral Stationary Phases
Finn, John Michael
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https://hdl.handle.net/2142/70188
Description
Title
Design, Synthesis, and Applications of Chiral Stationary Phases
Author(s)
Finn, John Michael
Issue Date
1982
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Abstract
Chemists who are engaged in the synthesis of optically active compounds frequently encounter the problems of assaying enantiomeric purity, assigning absolute configuration, and preparatively obtaining optical isomers in high enantiomeric purity. An almost ideal solution to all these problems would be the direct liquid chromatographic separation of the enantiomers upon a chiral stationary phase. The aim of this research was to develop efficient and widely useful chiral stationary phases. Our approach to this problem was to synthesize a series of specific chiral compounds containing three sites for potential use in chiral recognition. These compounds, when bound to a silica support, interact differentially with solute enantiomers in a consistent and predictable manner. By using very general types of interactions, chiral stationary phases were developed that are able to resolve enantiomers of solutes from a wide range of functional classes.
By stirring a THF solution of N-(3,5-dinitrobenzoyl)phenylglycine with an aminopropylsilanized silica gel, a widely useful, amino acid derived, chiral stationary phase was developed. This chiral stationary phase can be used as an analytical tool to assay enantiomeric purities and determine absolute configuration of several broad classes of solutes. Described in detail is the use of this chiral stationary phase in resolving the enantiomers of aryl carbinols, 3-aryl lactams, and aryl sulfoxides. On a preparative scale, the successful resolution of racemates in multigram quantities is described.
Also developed were a carbinol chiral stationary phase and two aryl sulfoxide chiral stationary phases. The utility of these chiral stationary phases in the resolution of enantiomers is described.
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