Potassium Carbonate → (R,R)-Stilbene oxide

Participants

Reaction Steps

Reaction at 0° C.: trans-Stilbene (0.181 g, 1 mmol) was dissolved in acetonitrile/DMM (15 mL, ½, V/V), subsequently were added buffer (10 mL, 0.05 M solution of Na2B4O7.H2O in 4×10−4 M aqueous Na2EDTA), tetrabutylammonium hydrogen sulfate (0.015 g, 0.04 mmol), and ketone 1 (0.0774 g, 0.3 mmol). The mixture was cooled by an ice bath. A solution of Oxone® (0.85 g, 1.38 mmol) in aqueous Na2EDTA (4×10−4 M, 6.5 mL) and a solution of K2CO3 (0.8 g, 5.8 mmol) in water (6.5 mL) were added dropwise separately over a period of 1.5 h (via syringe pumps or additional funnels). The reaction was then worked up by the same procedure as Method A to afford trans-stilbene oxide (0.153 g, 78% yield, 98.9% ee).

Provenance & Evidence