反应详情

Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and (E)-3-(4-chlorophenyl)acrylaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 12 as a white solid (78 mg, 58%). Analytical data for 12: 1H NMR (500 MHz, CDCl3) δ 9.37 (d, J=7.9 Hz, 1H), 7.89 (ddd, J=9.2, 6.1, 3.2 Hz, 1H), 7.38-7.31 (m, 2H), 7.31-7.26 (m, 3H), 7.12-6.92 (m, 6H), 4.08 (d, J=6.8 Hz, 1H), 3.56 (ddd, J=9.8, 6.9, 4.9 Hz, 1H), 3.29 (dd, J=14.9, 5.0 Hz, 1H), 2.43 (dd, J=14.9, 9.8 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 168.7, 159.11 (d, JCF=244.0 Hz), 155.38 (d, JCF=242.2 Hz), 148.9, 136.8, 136.5, 136.3, 132.6, 130.4, 129.3, 128.8, 128.4, 127.9, 118.32 (dd, JCF=12.4, 9.3 Hz), 117.12 (dd, JCF=25.5, 8.6 Hz), 116.64 (dd, JCF=24.8, 9.2 Hz), 114.51 (dd, JCF=26.9, 3.7 Hz), 110.69 (d, JCF=3.8 Hz), 47.2, 38.6, 32.3; IR (film) cm−1 1769, 1638, 1492, 1481, 1462, 1239, 1171, 1118, 1096, 1032, 813, 766, 741, 699; LRMS (ESI): Mass calcd for [M+H]+ C25H18ClF2N2O2: 451.1. found 451.3; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 5% IPA/3% MeOH/hexanes 0.5 mL/min, 280 nm), Rt1 (major)=40.5, Rt2 (minor)=50.6 min; er=98:2.

1. customPrepared
2. customThe unpurified residue was purified by flash chromatography