Abstract
The indium-mediated Reformatsky reaction of a mannose-derived lactone with α,α-disubstituted-α-bromo esters yielded the corresponding ulosonic acid esters as mixtures of anomers. In contrast, the reaction with α-monosubstituted-α-bromo esters is highly stereoselective and afforded a single anomer of the corresponding (2 S)-ulosonic acid esters. A mechanistic proposal for the reaction and an explanation of its outcome is discussed. The indium-mediated Reformatsky reaction of the mannose-derived lactone with 2-bromo-lactones was also achieved and the products obtained were consistent with those of our proposed mechanism in all cases. Moreover, indium-mediated allylation of the model sugar lactone was also investigated.
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