[C:1]([O-:4])([O-])=O.[K+].[K+].[C:7]1([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23]C=C)=[C:18]([Br:26])[CH:17]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O-]S([O-])=O.[Na+].[Na+].O.C[C:35]([OH:38])(C)C.O>CC(O)(C)C.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[C:7]1([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C@@H:1]([OH:4])[CH2:35][OH:38])=[C:18]([Br:26])[CH:17]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1A solution of potassium osmate dihydrate (1.19 mg, 0.0034 mmol), hydroquinidine (anthraquinone-1,4-diyl)diether (7.32 mg, 0.00851 mmol), potassium ferricyanide (843 mg, 2.55 mmol) and K2CO3 (357 mg, 2.55 mmol) in t-BuOH/H2O (3.5 mL/4.5 mL) was cooled to 0° C. and a solution of 4-benzenesulfonyl-2-bromo-1-but-3-enyl-benzene (299 mg, 0.851 mmol) in t-BuOH (1 mL) was added. The reaction was maintained at 0° C. for 18 hours, then Na2SO3 (0.68 g) was added at 0° C. The reaction was allowed to warm to room temperature and water was added. The mixture was extracted twice with EtOAc, and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash chromatography (hexane/EtOAc) to afford (R)-4-(4-benzenesulfonyl-2-bromo-phenyl)-butane-1,2-diol (193 mg) with 86% ee. Chiral column: Chiralpak AS analytical, hexane/isopropanol (75/25), 1.1 mL/min flow rate.
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