To tert-butyl carbamate (150 mg, 1.28 mmol) in n-propanol (1.75 mL) was added sodium hydroxide (49.8 mg, 1.25 mmol) in water (3.5 mL) followed by tert-butyl hypochlorite (0.141 mL, 1.246 mmol). After 5 min, the solution was cooled to 0° C. and treated with a solution of DHQD2(PHAL) (16.57 mg, 0.021 mmol) in n-propanol (1.75 mL). The reaction was diluted with n-propanol (3.5 mL) and treated with (E)-2-bromo-5-fluoro-4-(2-fluorostyryl)pyridine (90 mg, 0.304 mmol) as a solid in one portion. To this was added potassium osmate dihydrate (5.60 mg, 0.015 mmol) as a solid in one portion. The reaction was allowed to gradually warm to room temperature in the dewar overnight. The reaction was cooled to 0° C. and quenched by addition of sodium thiosulfate (150 mg) in water (3 mL). The ice bath was removed and stirring continued for 30 min. The reaction was diluted with ether, washed with water (3×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (25% EtOAc/Hex) gave 93 mg (36%) as a foam solid. Mass spec.: 429.1 (MH)+.
