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|Title:||Extension of Chromatographically - Derived Molecular Recognition Concepts to Stereoselective Reactions and Transformations|
|Author(s):||Reno, Daniel Scott|
|Department / Program:||Chemistry|
|Degree Granting Institution:||University of Illinois at Urbana-Champaign|
|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.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1987.
|Date Available in IDEALS:||2014-12-15|