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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

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dc.contributor.authorHo, Junming
dc.contributor.authorCoote, Michelle
dc.contributor.authorEaston, Christopher
dc.date.accessioned2015-12-10T22:53:18Z
dc.date.issued2011
dc.date.updated2016-02-24T10:24:25Z
dc.description.abstractTheoretical 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
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/1885/59291
dc.publisherAmerican Chemical Society
dc.sourceJournal of Organic Chemistry
dc.subjectKeywords: 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
dc.titleValidation 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
dc.typeJournal article
local.bibliographicCitation.issue15
local.bibliographicCitation.lastpage5914
local.bibliographicCitation.startpage5907
local.contributor.affiliationHo, Junming, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationCoote, Michelle, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationEaston, Christopher, College of Physical and Mathematical Sciences, ANU
local.contributor.authoruidHo, Junming, u4041618
local.contributor.authoruidCoote, Michelle, u4031074
local.contributor.authoruidEaston, Christopher, u9500570
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030701 - Quantum Chemistry
local.identifier.absfor030505 - Physical Organic Chemistry
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
local.identifier.ariespublicationu4005981xPUB483
local.identifier.citationvolume76
local.identifier.doi10.1021/jo200994z
local.identifier.scopusID2-s2.0-79961034485
local.identifier.thomsonID000293252600004
local.type.statusPublished Version

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