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

Bodkin, Jennifer A; Bacskay, George B; McLeod, Malcolm


An 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...[Show more]

CollectionsANU Research Publications
Date published: 2008
Type: Journal article
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/b803310b


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