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MeO
MeO2C Bz
N
H
58e
2-Benzoylamino-2-(4-methoxybenzyl)-penta-3,4-dienoic acid methyl ester (58e). Prepared by
following general procedure B with: 56e (24.1 g, 71.4 mmol), Et3N (41.7 mL, 300.0 mmol),
CCl4 (24.1 mL, 250.0 mmol), PPh3 (58 g, 221 mmol). Yield of 58e (17.5 g, 70%).
1 H NMR (300 MHz, CDCl3): δ 7.71-7.69 (m, 2H), 7.52-739 (m, 3H), 7.03 (d, J = 8.3 Hz, 2H),
6.84 (s, 1H), 6.76 (d, J = 8.2 Hz, 2H), 5.64 (t, J = 6.7 Hz, 1H), 5.00 (dd, J = 10.6, 6.7 Hz, 1H),
4.93 (dd, J = 11.1, 6.6 Hz, 1H), 3.83 (s, 3H), 3.75 (s, 3H), 3.71 (d, J = 13.9 Hz, 1H), 3.47 (d, J =
13.7 Hz, 1H); 13 C NMR (75 MHz, CDCl3): δ 206.8, 172.1, 166.5, 158.5, 134.6, 131.5, 131.1,
128.5, 127.6, 126.8, 113.5, 93.0, 80.1, 62.8, 55.0, 2.9, 39.1; IR (thin film): ν 3413, 2951, 1958,
1740, 1662, 1513, 1249 cm -1 ; MS m/z (%) 351 (10), 319 (7), 292 (12), 246 (27), 230 (60), 105
(100); EI-HRMS calcd for C21H21NO4 m/z [M] + 351.1471; found 351.1470.
F
MeO2C Bz
N
H
58f
2-Benzoylamino-2-(4-fluorobenzyl)-penta-3,4-dienoic acid methyl ester (58f). Prepared by
following general procedure B with: 56f (0.40 g, 1.23 mmol), Et3N (0.72 mL, 5.17 mmol), CCl4
(0.42 mL, 4.31 mmol), PPh3 (0.99 g, 3.81 mmol). Yield of 58f (270 mg, 65%).
1 H NMR (300 MHz, CDCl3): δ 7.70-7.67 (m, 2H), 7.51-7.39 (m, 3H), 7.09-7.04 (m, 2H), 6.92-
6.83 (m, 3H), 5.62 (t, J = 6.7 Hz, 1H), 5.03 (dd, J = 11.2, 6.6 Hz, 1H), 4.62 (dd, J = 11.2, 6.6 Hz,
1H), 3.83 (s, 3H), 3.75 (d, J = 13.7 Hz, 1H), 3.54 (d, J = 13.7 Hz, 1H); 13 C NMR (75 MHz,
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