Asymmetric synthesis of β-hydroxy sulfonic acids by BINAP/Ru-catalyzed hydrogenation

Article abstract of DOI:10.1016/S0040-4020(99)00443-3

BINAP/Ru(II) complexes catalyze enantioselective hydrogenation of sodium β-keto sulfonates in acidic methanol tinder atmospheric pressure of hydrogen at 50 °C to give the corresponding β-hydroxy sulfonates with up to 97% ee in a quantitative yield. The sense of asymmetric induction is predictable. The low-pressure hydrogenation process allows the hectogram-scale synthesis of a variety of optically active β-hydroxy sulfonates, which attract attention in connection with their functions as surfactants, catalysts, enzyme inhibitors, etc.