Extension of Chromatographically - Derived Molecular Recognition Concepts to Stereoselective Reactions and Transformations
Reno, Daniel Scott
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https://hdl.handle.net/2142/70394
Description
Title
Extension of Chromatographically - Derived Molecular Recognition Concepts to Stereoselective Reactions and Transformations
Author(s)
Reno, Daniel Scott
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
Analogues of chiral stationary phases (CSPs) and analogues of enantiomeric analytes separable upon the CSPs were employed in the investigation of stereoselective reactions and transformations. N-(3,5-dinitrobenzoyl)phenylglycine and N-(3,5-dinitrobenzoyl)leucine were used to study the stereochemical course of the coupling of chiral acids and chiral amines.
A chiral stationary phase precursor, an ester of N-(2-naphthyl)alanine, was used as a chiral solvating agent in the first-order asymmetric transformation of thioesters derived from N-acyl amino acids. Both sets of studies provided results which suggest that the interactions which afford differentiation of enantiomers during chromatographic separation on CSPs may also influence the stereochemical course of coupling reactions and asymmetric transformations.
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