tert-Butanol → (R)-2-(4-isobutylphenyl)-1,2-propanediol

Participants

Reaction Steps

The cathode compartment of the above described glass H-cell is charged with an aqueous solution of KH2PO4 (0.4M, 50 mL) and the anode is charged with the following: t-BuOH (50 mL), H2O (50 mL), K2CO3 (2.65 g, 20 mmol), K4Fe(CN)6.3H2O(0.633 g, 1.5 mmol). The solution is kept at 22° C. and the electrolysis is commenced at a controlled potential of 0.20-0.25 V (vs reference Ag/AgCl). After ca. 144 coulombs of electricity is consumed, the anode compartment is charged with the chiral ligand, MEQ-DHQD, (94 mg, 0.2 mmol), OsO4 in toulene (0.1 mL, 0.196M) and 2-(4-isobutylphenyl)propene (0.45 g, 2.5 mmol). After a total of 448 coulombs of electricity is further consumed, the reaction is stopped and is worked up as above to give the diol, (R)-2-(4-isobutylphenyl)-1,2-propanediol, in ca. 100% yield and 81.4% ee (crude ee by HPLC analysis on the chiracel OJ column).

Provenance & Evidence