Ethyl trans-beta-methylcinnamate → HCID 570672, compound

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Reaction Steps

According to the general procedure, a solution of ethyl 3-phenylbut-2-enoate (57 mg, 0.29 mmol) and iridium catalyst (S)-32 (9.4 mg, 0.0060 mmol, 2 mol %) in CH2Cl2 (3 mL) was hydrogenated. Removal of the solvent in vacuo and standard purification gave 34 (54 mg, 94%) as a colorless oil. [α]20D −55.2 (c 1.00, CHCl3); CSP HPLC analysis (Chiralcel OB-H; eluent: 99.5:0.5 hexanes/i-PrOH, 0.5 mL/min) determined a 95:5 er (90% ee) [tR(major) 11.99 min, tR(minor) 14.09 min]; 1H NMR (300 MHz, CDCl3) 7.33-7.17 (m, 5H), 4.08 (q, 2H, J=6.9 Hz), 3.35-3.23 (sextet, 1H, J=7.2 Hz), 2.66-2.50 (m, 2H), 1.31 (d, 3H, J=6.9 Hz), 1.19 (t, 3H, J=6.9 Hz) ppm; 13C NMR (75 MHz, CDCl3) 172.4, 145.7, 128.4, 126.7, 126.3, 60.2, 43.0, 36.5, 21.8, 14.1 ppm.

Provenance & Evidence