Validation of the distal effect of electron-withdrawing groups on the stability of peptide enolates and its exploitation in the controlled stereochemical inversion of amino acid derivatives
Date
2011
Authors
Ho, Junming
Coote, Michelle
Easton, Christopher
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Publisher
American Chemical Society
Abstract
Theoretical studies had predicted that N-electron-withdrawing substituents, hydrogen bonding, and protonation at amide nitrogen selectively increase the acidity of a distal proton adjacent to the amide carbonyl to the extent that the α-carbonyl acidity o
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Keywords: Amino acid derivatives; Deuterations; Diastereomers; Diketopiperazines; Electron withdrawing group; Enolates; Hydrogen-deuterium exchange; N-methylamino acid; Orders of magnitude; Stereochemical inversion; Strong correlation; Theoretical study; Acidity; A
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Source
Journal of Organic Chemistry
Type
Journal article
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2037-12-31
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