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