P(=O)(O)(O)O.C([O-])([O-])=[O:7].[K+].[K+].[CH3:12][C:13]([OH:16])([CH3:15])[CH3:14].[CH3:17][C:18]([C:20]1C=CC=[CH:22][CH:21]=1)=C>O=[Os](=O)(=O)=O.O>[C:12]1([C@:13]([OH:16])([CH3:15])[CH2:14][OH:7])[CH:22]=[CH:21][CH:20]=[CH:18][CH:17]=1
The cathode compartment of a divided glass H-cell as described in Example 6.1 is charged with 40 mL of 10% phosphoric acid, and the anode compartment is charged with Na4Fe(CN)6.10H2O (3.9 g, 8.0 mmol), K2CO3 (8.3 g, 60 mmol) and t-BuOH (50 mL)/water (50 mL), the chiral ligand, PHAL-DHQD (878 mg. 0.10 mmol), OsO4 (0.196M in toluene, 0.05 mL, 0.01 mmol) and α-methylstyrene (2.4 g, 20 mmol). The mixture is electrolyzed at 0.4 V (vs ref. Ag/AgCl) at 15° C. until about 4253 coulombs of electricity is consumed. After stirring without electricity for 4 hours, the reaction is worked up as in Example 6.1 to give (R)-2-phenyl-1,2-propanediol (2.87 g, 94.5% yield and 92.6% ee).
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