Phosphoric Acid → (R)-2-phenyl-1,2-propanediol

Participants

Reaction Steps

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 (0.196 M 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.I to give (R)-2-phenyl-1,2-propanediol (2.87 g, 94.5% yield and 92.6% ee).

Provenance & Evidence