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Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone

Ma, Xinghua; Liu, Xin; Yates, Patrick; Raverty, Warwick; Banwell, Martin; Ma, Chenxi; Willis, Anthony; Carr, Paul D.


The manipulation of the enone moiety associated with the biomass-derived, homochiral and now abundant compound levoglucosenone (1) is described. While the trichloroacetimidates derived from the allylic alcohols 3 and 4 failed to engage in Overman-type rearrangements, certain ester derivatives reacted in the presence of Pd[0]-catalysts to give regio-isomeric mixtures of β,γ-unsaturated malonates or ketones, the structures of which were confirmed by single-crystal X-ray analyses. In other...[Show more]

CollectionsANU Research Publications
Date published: 2018-03-24
Type: Journal article
Source: Tetrahedron
DOI: 10.1016/j.tet.2018.03.023


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