Ethyl 2-methyl-3-phenyl-2-propenoate → Ethyl 2-methyl-3-phenylpropanoate

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Reaction Steps

According to the general procedure, a solution of ethyl 2-methyl-3-phenylacrylate (34 mg, 0.18 mmol) and iridium catalyst (S)-32 (5.7 mg, 0.0036 mmol, 2.0 mol %) in CH2Cl2 (1.8 mL) was hydrogenated. Removal of the solvent in vacuo and standard purification gave 36 (30 mg, 88%) as a colorless oil. [α]20D +28.4 (c 1.0, CHCl3); CSP HPLC analysis (Chiralcel OB-H; eluent: 99.5:0.5 hexanes/i-PrOH, 0.5 mL/min) determined a 91:9 er (82% ee) [tR(minor) 8.52 min, tR(major) 10.10 min]; 1H NMR (300 MHz, CDCl3) 7.31-7.16 (m, 5H), 4.09 (q, 2H, J=6.9 Hz), 3.08-2.98 (m, 1H), 2.79-2.64 (m, 2H), 1.21 (d, 3H, J=7.2 Hz), 1.16 (d, 3H, J=6.3 Hz) ppm; 13C NMR (75 MHz, CDCl3) 176.1, 139.4, 128.9, 128.3, 126.2, 60.2, 41.4, 39.7, 16.7, 14.1 ppm.

Provenance & Evidence