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Using a catalytic organosuperbase and a silane additive, the corresponding difluoroenolate could be generated and trapped with aldehydes to deliver various \u03b1,\u03b1\u2010difluoro\u2010\u03b2\u2010hydroxy ketones in high yields. This new strategy tolerates numerous functional groups and represents the access to the difluoroenolate by direct deprotonation of the difluoromethyl unit. The diastereoselective version of the reaction was also investigated with<jats:italic>d.r<\/jats:italic>. up to 93\u2009:\u20097. Several transformations were performed to demonstrate the synthetic potential of these \u03b1,\u03b1\u2010difluoro\u2010\u03b2\u2010hydroxy ketones. 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