α-Hydroxylation of carbonyls using iodine

The α-hydroxylation of ketones and aldehydes to α-hydroxyketals mediated by iodine under basic conditions in MeOH is described. Enolates generated under the reaction conditions are iodinated and the resulting α-iodocarbonyl is transformed into the hydroxyketal. The use of iodine for this chemistry represents an economical and practical alternative to existing methods for this transformation.