Enantioselective Reduction of Acetophenone

A 1 mL vial, under inert atmosphere, was filled with NaOH (1.0 mg, 25 μmol), acetophenone (12 μL, 100 μmol), and a solution of ruthenium complex 9 (1.3 mg, 1 μmol) in ⁱPrOH (0.125 mL, 1.63 mmol, around 16 equiv./ketone). The reaction mixture was heated for 1 h. The solution was diluted with 0.2 mL of CH₂Cl₂ and passed through a Millipore filter. An aliquot was analyzed by GC with a Chirasil-DEX CB column (25 m × 0.25 mm) (Agilent Technologies, Santa Clara, CA, USA) to determinate the enantiomeric excess. The remaining solution was concentrated under vacuum and the resulting crude solution was analyzed by ¹H NMR spectroscopy to determinate the conversion.