Direct Liquid Chromatographic Separation of Enantiomers of Phthalides, Phthalimidines and Related Compounds on Chiral Stationary Phases
Sowin, Thomas Joseph
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https://hdl.handle.net/2142/70365
Description
Title
Direct Liquid Chromatographic Separation of Enantiomers of Phthalides, Phthalimidines and Related Compounds on Chiral Stationary Phases
Author(s)
Sowin, Thomas Joseph
Issue Date
1987
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
The enantiomers of a diverse series of 3-arylphthalides are separable by high performance liquid chromatography on chiral stationary phases (CSPs) derived from the N-3,5-dinitrobenzamides of (S)-leucine or (R)-phenylglycine covalently bonded to aminopropyl silanized silica. A chiral recognition model for the separation of phthalide enantiomers has been formulated based on the observed chromatographic behavior of these phthalides. Assignment of elution orders based on the a priori model proposed are consistent with those ultimately determined by independent chemical and spectroscopic means. A phthalide structurally optimized to maximize the chromatographic separability of its enantiomers on the aforementioned CSPs is incorporated into a phthalide-based CSP which has proven to be effective for the separation of enantiomers of numerous analytes. The chromatographic behavior of a variety of 3-arylphthalimidines and their corresponding ureide derivatives on the amino acid CSPs, as well as a novel procedure for C-3 alkylation without N-2 alkylation of these phthalimidines via conversion to the ureide derivatives, is described. Alkylation of certain enantiomerically pure ureides affords enantiomerically enriched products owing to the self-immolative transfer of chirality from central to axial, back to central chirality. Factors affecting this process are discussed.
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