Ho, JunmingCoote, MichelleEaston, Christopher2015-12-100022-3263http://hdl.handle.net/1885/59291Theoretical 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 oKeywords: 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; AValidation 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 derivatives201110.1021/jo200994z2016-02-24