The catalytic asymmetric aldol reaction of pyruvic aldehyde dimethyl acetal and 2-acetylthiazole with sugar aldehydes is demonstrated to be the key step in the synthesis of 3-deoxy- 2-ulosonic acids. Efficient and stereoselective pyruvate aldol reactions are catalyzed by metal-based chiral Trost and Shibasaki catalysts. The presented synthetic methodology mimics aldolase-catalyzed reactions by direct activation of C 3 pyruvate equivalents with the use of metal-based chiral cata- lysts en route to the synthesis of 2-keto-3-deoxy- D -glucosonic acid and 3-deoxy- D -manno-2-octulosonic acid derivatives.