Abstract:Ferrier reactions follow a mechanistic pathway whereby
Lewis acid
activation of a cyclic enol ether facilitates departure of an allylic
leaving group to form a glycosyl Ferrier cation. Attack on the Ferrier
cation provides a new acetal linkage concurrent with the transposition
of the alkene moiety. The idiosyncratic outcomes of Ferrier reactions
of seven-membered ring carbohydrate-based oxepines prompted an investigation
of its corresponding septanosyl Ferrier cation. Experiments that characterized
the ion, in… Show more
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