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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

Ho, Junming; Coote, Michelle; Easton, Christopher

Description

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

CollectionsANU Research Publications
Date published: 2011
Type: Journal article
URI: http://hdl.handle.net/1885/59291
Source: Journal of Organic Chemistry
DOI: 10.1021/jo200994z

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