Direct Aldol Reaction of Pyruvic Derivatives: Catalytic Attempt To Synthesize Ulosonic Acids

Abstract

AbstractThe 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 C3 pyruvate equivalents with the use of metal‐based chiral catalysts en route to the synthesis of 2‐keto‐3‐deoxy‐D‐glucosonic acid and 3‐deoxy‐D‐manno‐2‐octulosonic acid derivatives.