1-phenylpropane-1,2-diol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3.5 ml of a water-acetone (1:1) solvent were added 66.6 mg of the osmium oxide carried by the carrier of the present invention obtained in Example 4, 21.5 mg of 1,4-bis(9-o-dihydroquinidil)phthalazine, 362.2 mg of potassium ferricyanide and 152.0 mg of potassium carbonate, followed by reacting at 30° C. for 1 hour while stirring. And 59.0 mg of trans-β-methylstyrene dissolved in 1.5 ml of a water-acetone (1:1) solvent were added to the reaction solution and followed by reacting for another 2 hours while stirring. And further, 362.2 mg of potassium ferricyanide and 152.0 mg of potassium carbonate were added to the reaction solution and followed by reacting for another 2 hours while stirring. After the reaction was terminated by adding methanol, the filtrate obtained by filtrating the reaction solution was concentrated to some extent. The obtained product was dissolved in 5 ml of methylene chloride and filtrated using Celite. The filtrate was concentrated and purified using a silica gel thin-layer chromatography, to obtain 70.6 mg of a desired diol, 1-phenyl-1,2-propane diol (yield 85%) (97% ee). were added to the reaction solution by reacting for another 2 hours while stirring by reacting for another 2 hours while stirring After the reaction was terminated by adding methanol the filtrate obtained by filtrating the reaction solution was concentrated to some extent The obtained product was dissolved in 5 ml of methylene chloride filtrated The filtrate was concentrated purified