[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=C)=[CH:4][CH:3]=1.[NH+]1([O-])[CH2:15][CH2:14][O:13]CC1.S([O-])([O-])(=[O:19])=S.[Na+].[Na+]>CC(C)=O.O.O=[Os](=O)(=O)=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:14]([OH:13])[CH2:15][OH:19])=[CH:4][CH:3]=1To 4-bromostyrene (Compound [LXI], 366 mg, 2 mmol, 1 eq.) in acetone (10 mL) was added morpholine N-oxide (953 mg of a 50% solution in H2O, 4.0 mmol, 2.0 eq.) and then OsO4 (1.3 g for a 4% OsO4 in H2O, 0.2 mmol, 0.1 eq). The mixture was allowed to stir at room temperature for 1 hour. The reaction mixture was then added to an aqueous solution of sodium thiosulfate and then extracted three times with EtOAc. The combined organics were dried over Na2SO4, concentrated, and subjected to silica gel chromatography using EtOAc-heptane as the eluant to provide Compound [LXII]: 1H NMR (400 MHz, METHANOL-d4) δ ppm 3.54-3.66 (m, 2H) 4.66 (dd, J=6.76, 5.10 Hz, 1H) 7.24-7.35 (m, 2H) 7.41-7.53 (m, 2H).
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