Download (3249Kb) - D-Scholarship@Pitt - University of Pittsburgh

Hz, 1H), 2.86-2.79 (m, 1H), 2.82 (d, J = 16.8 Hz, 1H), 1.23 (d, J = 7.4 Hz, 1H), -0.14 (s, 9H).
13 C NMR (75 MHz, CDCl3): δ 210.2, 171.7, 171.6, 165.5, 142.8, 138.2, 136.3, 136.0, 130.6,
130.0, 128.9, 128.4, 127.3, 126.3, 121.5, 65.7, 53.2, 46.4, 42.9, 40.0, 13.8, -1.3; IR (thin film): ν
2952, 1742, 1694, 1647, 1250 cm -1 ; MS m/z (%) 473 (5), 458 (22), 382 (45), 105 (100); EI-
HRMS calcd for C28H31NO4Si m/z [M] + 473.2022; found 473.2033.
270c (minor diastereomer – eluting second): 1 H NMR (300 MHz, CDCl3): δ 7.45-7.42 (m, 3H),
7.34-7.31 (m, 2H), 7.27-7.24 (m, 3H), 7.19-7.16 (m, 2H), 5.77 (d, J = 1.0 Hz, 1H), 4.39 (d, J =
18.5, 1.2 Hz, 1H), 4.15 (d, J = 13.7 Hz, 1H), 3.83 (s, 3H), 3.38 (d, J = 13.7 Hz, 1H), 2.94 (d, J =
18.5 Hz, 1H), 2.80 (q, J = 7.6 Hz, 1H), 1.29 (d, J = 7.5 Hz, 3H), -0.15 (s, 9H); 13 C NMR (75
MHz, CDCl3): δ 210.0, 171.7, 171.5, 165.8, 142.2, 138.0, 136.0, 130.7, 129.9, 128.8, 128.1,
127.2, 126.2, 121.5, 65.5, 53.0, 46.7, 42.5, 39.9, 14.2, -1.5; IR (thin film): ν 2953, 1742, 1695,
1649, 1250 cm -1 ; MS m/z (%) 473 (5), 458 (22), 382 (45), 105 (100); EI-HRMS calcd for
C28H31NO4Si m/z [M] + 473.2022; found 473.2042.
Bz
MeO 2C
2-Benzoyl-3-benzyl-5-methyl-6-oxo-7-phenyl-2,3,5,6-tetrahydro-1H-[2]pyrindine-3-
carboxylic acid methyl ester (270d). Prepared by following general procedure N, using:
N
Bn
73d (37 mg, 82 µmol), [Rh(CO)2Cl]2 (3 mg, 8 µmol), PPh3 (6 mg, 25 µmol), AgBF4 (180 µL of
0.1 M solution in DCE, 18 µmol). The reaction was heated at 35 °C for 1 h.
Yield 270d (29 mg, 74%) as a mixture of diastereomers in ratio 1.6 : 1. The diastereomers were
separated by semi-preparative HPLC (hexanes/EtOAc, 5 : 1, v/v, flow rate 3 mL/min, UV
detector at 254 nm).
270d (major diastereomer, Rt = 15 min, HPLC, hexanes/EtOAc, 5 : 1, v/v): 1 H NMR (300 MHz,
270d
238
Ph
O