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

BINAP/Ru(II) complexes catalyze enantioselective hydrogenation of sodium be ta-keto sulfonates in acidic methanol under atmospheric pressure of hydroge n at 50 degrees C to give the corresponding beta-hydroxy sulfonates with up to 97% ee in a quantitative yield. The sense of asymmetric induction is pr edictable. The low-pressure hydrogenation process allows the hectogram-scal e synthesis of a variety of optically active beta-hydroxy sulfonates, which attract attention in connection with their functions as surfactants, catal ysts, enzyme inhibitors, etc. (C) 1999 Elsevier Science Ltd. All rights res erved.