[C:1]([CH2:9][C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(O)=O>CC1C=CC(C(C)C)=CC=1.CC1C=CC(S([N-][C@H]([C@@H](N)C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)=CC=1.[Cl-].[Ru+2].O>[OH:8][C@H:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]#[N:11]A 50 ml Schlenk flask was charged with 7.26 g (50.0 mmol) of benzoylacetonitrile, 18.1 ml (130 mmol) of triethylamine, 5.8 ml (155 mmol) of formic acid, and 31.8 mg (0.05 mmol, S/C=1000) of RuCl[(S,S)-Tsdpen](p-cymene) under an atmosphere of argon, and stirring was carried out at 30° C. for 24 hours. The solution was poured into water and extracted with ether, the organic layer was washed with saturated brine and then dried with anhydrous sodium sulfate, and the solvent was distilled off under vacuum. The crude product so obtained was distilled under vacuum (0.4 mmHg, 145° C.) to give 6.34 g (yield 86%, 1H-NMR) of (S)-3-hydroxy-3-phenylpropanenitrile. When this was analyzed using a CHIRALCEL OJ column (manufactured by Daicel Chemical Industries, Ltd., eluant; n-hexane:2-propanol=20:1) it was found that the optical purity was 98% ee.
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