Abstract
AbstractCyanuric chloride activated dimethyl sulfoxide (DMSO) was found to catalyze the hydration of glycals and the hydrolysis of enol ethers, esters, oximes, O‐methyl oximes, and hydrazones. Overall, 68 examples of these 6 types of substrates were efficiently transformed into 2‐deoxysugars, phenols, and carbonyl compounds. Methyl methylene sulfonium chloride (a bulky weak Lewis acid) is presumed to be the active catalytic species. This assumption is strongly supported by the fact that the same reactions catalyzed by chloromethyl methyl sulfide/KI gave similar results to those catalyzed by the cyanuric chloride activated DMSO. We further employed the chloromethyl methyl sulfide/KI precatalyst to carbohydrate benzylidenations, decanal acetalizations, and the stereoselective transformations of 2‐deoxy‐2‐iodo‐α‐d‐mannopyranosyl acetate into 2,3‐unsaturated O‐glycosides. Key features of this precatalyst include that it is water tolerant, cost‐effective, and easily removed during workup.
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