Potassium Carbonate → (1S,2S)-(-)-1-Phenylpropylene oxide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Reaction at −10° C.: trans-β-methylstyrene (0.181 g, 1 mmol) was dissolved in acetonitrile/DMM (15 mL, ½, V/V). Buffer (10 mL, 0.05 M solution of Na2B4O7.H2O in 4×10−4 M aqueous Na2EDTA), tetrabutylammonium hydrogen sulfate (15 mg, 0.04 mmol), and ketone 1 (0.0774 g, 0.3 mmol) were added with stirring. The mixture was cooled to about −10° C. via a NaCl-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 2 h (via syringe pumps or addition funnels). The reaction was then worked up by the same procedure as Method B to afford trans-β-methylstyrene oxide (0.126 g, 94% yield, 95.5% ee).

Herkunft & Nachweise