(R)-(-)-p-Toluenesulfinamide

Experimental procedure (1 to 2): In a flask equipped with argon is placed a solution of THF (100 mL) and NaHMDS (1.0 mol/L solution in THF, 148 mL, 148 mmol, 6 eq.) at -78 °C. Methyl acetate (7.85 mL, 98.8 mmol, 4 eq.) in THF (20 mL) is added slowly, and the solution is stirred for 1 h. At this time anhydrous ether (20 mL) and 1 (7.48 g, 24.7 mmol, 1 eq.) in THF (20 mL) are added. The reaction mixture is stirred at -78 °C for 3.5 h and quenched with sat. NH₄Cl (50 mL). The solution is washed with ethyl acetate (3 x 150 mL), the organic phases are combined, dried (Na₂SO₄), and concentrated. Purification by flash chromatography (50% EtOAc/hexane) gives 2 (8.80 g, 85% yield) as an oil.