3.2. General Experimental Procedure for the Kinetic Resolution with or without an External Nucleophile

In an argon filled glovebox, an oven-dried resealable tube equipped with a magnetic stir bar was charged with the Ru-catalyst (0.1–0.25 mol%), racemic allylic alcohol (0.2 mmol), an amine nucleophile (0.12 mmol) or without an external nucleophile, toluene (2.0 mL), and dichloromethane (20 μL). t-BuOK (30 μL, 1.0 M in t-BuOH) was added into the above reaction mixture. After reaching a 45% to 65% conversion, the reaction was quenched by H₂O and extracted with ethyl acetate (3 × 5 mL). The combined organic layers were dried over Na₂SO₄ and concentrated under reduced pressure. The 1,4-dinitrobenzene (8.4 mg, 0.05 mmol) was added into the crude residue as the internal standard to determine the crude ¹H NMR yield of the recovered allylic alcohol. The reaction conversion (c) was calculated by the following formula: c = 1 − (¹H NMR yield_{(recovered alcohols)})%. The enantiomeric excess (ee) of the recovered allylic alcohol was determined by HPLC analysis. The selectivity factor (s) of the kinetic resolution was thus calculated by the formula: s = In[(1 − c)(1 − ee)]/In[(1 − c)(1 + ee)].