ChemInform Abstract: Scandium Trifluoromethanesulfonate-Catalyzed Cleavage of Esters Bearing a Coordinative Group at a Vicinal Position

Scandium trifluoromethanesulfonate is found to be a Lewis acid catalyst for selective cleavage of esters containing a coordinative group adjacent to an ester moiety. The reaction proceeds under weak acidic conditions at room temperature; the catalyst can be recovered and reused. Even α-acyloxy ketones are deacetylated without racemization. Selective monodeacetylation at C-10 of paclitaxel has been achieved.