Acetic Acid → HCID 118676928, compound

Participants

Reaction Conditions

Reaction Steps

N1,N2-bis(2-((R)-4-isopropyl-4,5-dihydrooxazol-2-yl)phenyl)benzene-1,2-diamine (6.95 mg, 0.014 mmol) and Mn(OTf)2 (5.09 mg, 0.014 mmol; for synthesis and application of this ligand see: Dai. W. et al. Org. Lett. 2013, 15, 5658; Dai. W. et al. Org. Lett. 2013, 15, 4138) in dichloromethane (10 mL) were stirred at room temperature for 3 h. 333a) (0.3 g, 0.721 mmol), acetic acid (0.263 mL, 4.61 mmol) and 30% aqueous hydrogen peroxide solution (0.147 mL, 1.47 mmol) were added at room temperature and the resulting mixture was immediately cooled with an ice bath to 5-8° C. The reaction mixture was stirred at this temperature for 30 min, quenched with saturated sodium sulfite solution (10 mL) and further stirred for 15 min. The mixture was then diluted with dichloromethane (30 mL) and washed with brine (20 mL). The combined organic layers were dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography [silica; dichloromethane with 1.5% methanol]. White solid. Yield: 0.14 g (45% of theory). Enantiomeric excess: >99% (chiral HPLC)

Provenance & Evidence