Potassium Carbonate → HCID 57723960, compound

Participants

Reaction Steps

To a solution of racemic cis-2,2-dimethyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (100 mg. 0.58 mmol) in 4 mL of H2O-tert-BuOH (1:1), were added sequentially K3Fe(CN)6 (580 mg, 1.76 mmol), K2CO3 (243 mg, 1.76 mmol), MeSO2NH2 (110 mg, 1.16 mmol) and (DHQD)2PHAL (60 mg, 0.08 mmol) at 0° C. The solution was stirred for 5 min and OsO4 (10 μL, 25 wt % in tert-BuOH) was added and stirring was maintained for 62 H at ambient temperature. Na2SO3 (100 mg) was added and the mixture was stirred for 30 min, filtered through filter paper and extracted with EtOAc—H2O (4:1 v/v, 100 mL×2). The combined organic layer was washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography with 100% EtOAc.

Provenance & Evidence