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(435 mg, 1.21 mmol), DMSO (429 µL, 6.06 mmol), Mo(CO)6 (400 mg, 1.51 mmol). Heated to
90 °C for 20 min. The crude mixture was purified by flash chromatography (gradient elution,
hexanes-EtOAc, 19 : 1 to 2 : 1, v/v) to afford 287b (260 mg, 55%). The correct product ratios
listed in Scheme 4.30 were determined in a separate experiment by integration of the olefinic
resonances in the 1 H NMR spectrum taken after complete removal of all volatiles from a small
reaction sample.
287b: 1 H NMR (300 MHz, CDCl3): δ 7.52-7.27 (m, 10H), 6.19 (s, 1H), 6.07 (s, 1H), 5.63 (s,
1H), 4.24 (d, J = 14.9 Hz, 1H), 4.23 (d, J = 14.2 Hz, 1H), 4.03 (d, J = 15.0 Hz, 1H), 3.98 (s, 1H),
3.62 (s, 3H), 3.39 (d, J = 14.3 Hz, 1H); 13 C NMR (75 MHz, CDCl3): δ 195.2, 170.9, 170.2,
170.1, 140.6, 135.7, 135.5, 131.1, 128.6, 128.5, 127.3, 126.2, 118.0, 70.8, 52.3, 51.5, 50.9, 37.7;
IR (thin film): ν 3027, 1741, 1710, 1641, 1383 cm -1 ; MS m/z (%) 387 (15), 328 (10), 282 (22),
105 (100); EI-HRMS calcd for C24H21NO4 m/z [M] + 387.1471 found 387.1470.
Bz
N
Bn
MeO2C 289b
2-Benzoyl-3-benzyl-6-oxo-2,3,5,6-tetrahydro-1H-[2]pyrindine-3-carboxylic acid methyl
ester (289b). 1 H NMR (300 MHz, CDCl3): δ 7.49-7.41 (m, 3H), 7.34-7.27 (m, 5H), 7.21-7.17
(m, 2H), 5.90 (s, 1H), 5.70 (s, 1H), 4.39 (d, J = 18.1 Hz, 1H), 4.15 (d, J = 13.8 Hz, 1H), 3.81 (s,
3H), 3.38 (d, J = 13.8 Hz, 1H), 3.05 (s, 2H), 3.01 (d, J = 18.1 Hz, 1H); 13 C NMR (75 MHz,
CDCl3): δ 202.9, 171.3, 171.1, 161.1, 135.8, 135.4, 135.2, 130.3, 129.9, 128.7, 128.3, 127.4,
127.2, 126.3, 123.5, 65.9, 53.0, 45.1, 39.6, 37.7; IR (thin film): ν 2950, 1740, 1710, 1643, 1391
cm -1 ; MS m/z (%) 387 (47), 356 (15), 328 (12), 296 (30), 105 (100); EI-HRMS calcd for
C24H21NO4 m/z [M] + 387.1471 found 387.1489.
247
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