The Sharpless asymmetric aminohydroxylation reaction: optimising ligand/substrate control of regioselectivity for the synthesis of 3- and 4-aminosugars

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dc.contributor.authorBodkin, Jennifer A.
dc.contributor.authorBacskay, George B.
dc.contributor.authorMcLeod, Malcolm
dc.date.accessioned2015-12-10T22:20:13Z
dc.date.issued2008
dc.date.updated2015-12-09T08:44:50Z
dc.description.abstractAn investigation of the factors responsible for the sense and magnitude of regioselectivity in the Sharpless asymmetric aminohydroxylation (AA) has been conducted. Theoretical investigations of ligand-osmium binding geometry and experimental investigations of the Sharpless AA reaction on a series of functionalized pent-2-enoic acid ester substrates demonstrate that the opposite regioselectivity afforded using PHAL and AQN ligands results from a change in substrate orientation with respect to the catalyst. Two distinct ligand binding domains within the catalyst have been proposed that undergo attractive interactions with the substrates. Selective access to each of the four potential regio- and stereo-isomeric AA products could be achieved through the appropriate choice of ligand and substrate. These results have been applied toward the efficient stereoselective synthesis of naturally occurring and regioisomeric 3- and 4-aminosugar derivatives.
dc.identifier.issn1477-0520
dc.identifier.urihttp://hdl.handle.net/1885/51830
dc.publisherRoyal Society of Chemistry
dc.sourceOrganic and Biomolecular Chemistry
dc.subjectKeywords: Addition reactions; Biochemistry; Catalysis; Esters; Hydroxylation; Ligands; Organic compounds; Osmium; Regioselectivity; Stereochemistry; Stereoselectivity; Sugars; acid esters; Aminohydroxylation; Applied (CO); Attractive interactions; binding geometrie
dc.titleThe Sharpless asymmetric aminohydroxylation reaction: optimising ligand/substrate control of regioselectivity for the synthesis of 3- and 4-aminosugars
dc.typeJournal article
local.bibliographicCitation.issue14
local.bibliographicCitation.lastpage2553
local.bibliographicCitation.startpage2544
local.contributor.affiliationBodkin, Jennifer A, University of Sydney
local.contributor.affiliationBacskay, George B, University of Sydney
local.contributor.affiliationMcLeod, Malcolm, College of Physical and Mathematical Sciences, ANU
local.contributor.authoremailu4045340@anu.edu.au
local.contributor.authoruidMcLeod, Malcolm, u4045340
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB233
local.identifier.citationvolume6
local.identifier.doi10.1039/b803310b
local.identifier.scopusID2-s2.0-46749150070
local.identifier.thomsonID000257424800013
local.identifier.uidSubmittedByu4005981
local.type.statusPublished Version

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