Enantioselective Adsorption of 1,3-Dithiolane-1-Oxides and Related Compounds on Liquid Chromatographic Amino Acid-Derived Chiral Stationary Phases (Resolution, Enantiomers, Sulfoxides)
Hamper, Bruce Cameron
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https://hdl.handle.net/2142/70273
Description
Title
Enantioselective Adsorption of 1,3-Dithiolane-1-Oxides and Related Compounds on Liquid Chromatographic Amino Acid-Derived Chiral Stationary Phases (Resolution, Enantiomers, Sulfoxides)
Author(s)
Hamper, Bruce Cameron
Issue Date
1984
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
Chiral stationary phases derived from N-3,5-dinitrobenzoyl amino acids such as (R)-phenylglycine, (S)-leucine, (S)-phenylalanine and (S)-valine bonded to aminopropyl silanized silica are employed for preparative and analytical liquid chromatographic separation of the enantiomers of 1,3-dithiolane-1-oxides and related compounds. The structure-enantioselectivity relationships allow determination of two fundamental chiral recognition models for resolution of enantiomeric analytes which, in turn, allow assignment of the absolute configuration of many cyclic sulfoxides on the basis of chromatographic elution order. Confirmation of these assignments is provided by circular dichroism spectroscopy, NMR spectroscopy in the presence of a chiral solvating agent and preparation of chiral sulfoxides from compounds of known absolute configuration. The chiral recognition models are useful for determining the essential functionality required for enantioselective adsorbtion to occur and may be employed for assignment of absolute configuration of many classes of compounds. Lacinilene C and lacinilene C methyl ether are chromatographically resolved and the absolute configurations determined by chromatographic elution order, circular dichroism and NMR spectroscopy in the presence of chiralsolvating agents.
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