give 7 (1.31 g, 94%) as a colorless oil: IR (CHCl3) υ 1682 cm-1; rotamers of 7 were
1
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1
observed by H NMR and C NMR. H NMR (500 MHz, CDCl3) δ 1.18 (9H, s), 3.11
(1H, br-t, J = 12.5 Hz), 3.28 (1H, br-d, J = 12.0 Hz), 3.73 (3H, br-s), 3.88 (3H, br-s),
4.17, 4.32 (total 2H, both br), 5.36 (1H, br-s), 5.50 (1H, s), 5.60-5.71 (1H, m), 6.43-7.20
(12H, m); 13C NMR (125 MHz, CDCl3) δ 28.1, 41.9, 46.5, 55.1, 56.5, 56.9, 79.5, 93.9,
109.0, 112.9, 115.4, 119.2, 123.4, 126.4, 127.3, 127.8, 128.2, 128.7, 128.8, 139.3, 141.8,
143.4, 158.1, 159.4; HRMS calcd for C30H34NO4I 599.1533, found: 599.1530.
N-Benzyl-N-[1-(2-iodo-3-methoxyphenyl)-3-(3-methoxyphenyl)]but-3-en-
2-yl-2-phenylacrylamide (8). To a solution of 7 (1.25 g, 2.09 mmol) in CH2Cl2 (8 mL)
was added trifluoroacetic acid (8 mL) at 0 °C, and the mixture was further stirred at the
same temperature for 1 h. The reaction mixture was basified with a saturated NaHCO3
solution and extracted with CH2Cl2, and the organic layer was washed with brine. After
drying (MgSO4), the mixture was concentrated to give crude amine as a brown oil. To a
solution of the crude material, triethylamine (633 mg, 6.26 mmol) and
N,N-dimethylaminopyridine (128 mg, 1.04 mmol) in CH2Cl2 (20 mL) were added
cinnamoyl chloride (522 mg, 3.13 mmol) at 0 °C, and the mixture was further stirred at
room temperture for 2 h. The reaction mixture was diluted with a saturated NaHCO3
solution and extracted with CH2Cl2, and the organic layer was washed with brine. After
drying (MgSO4), the mixture was concentrated and chromatographed on silica gel
(hexane/AcOEt, 4:1) to give 8 (1.16 g, 89%) as a colorless amorphous solid: IR (CHCl3)
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υ 1601, 1646 cm-1; rotamers of 8 were observed by H NMR and C NMR. H NMR
(500 MHz, CDCl3) δ 3.19 (2/3H, dd, J = 13.4, 10.7 Hz), 3.30 (1/3H, dd, J = 13.4, 10.7
Hz), 3.33 (1/3H, s, dd, J = 13.4, 10.7 Hz), 3.45 (2/3H, dd, J = 13.7, 2.4 Hz), 3.51 (2/3 ×
3H, s), 3.62 (2/3 × 3H, s), 3.76 (1/3 × 3H, s), 3.85 (1/3 × 3H, s), 4.55-4.58 [(1 + 1/3)H,
m], 4.67 (2/3H, d, J = 14.6 Hz), 5.35 (1/3H, s), 5.56 (2/3H, s), 5.58 (1/3H, s), 5.63
(2/3H, s), 6.28 (2/3H, d, J = 7.6 Hz), 6.34 (2/3H, d, J = 15.1 Hz), 6.39-6.46 (1H, m),
6.53 (1/3H, d, J = 15.1 Hz), 6.63-7.33 (17H, m), 7.56 (1/3H, d, J = 15.1 Hz); 13C NMR
(125 MHz, CDCl3) δ 42.2, 42.4, 45.9, 48.3, 55.0, 55.2, 56.0, 56.4, 58.9, 93.2, 108.9,
109.5, 111.8, 112.1, 113.9, 114.1, 116.8, 116.9, 117.4, 118.7, 118.9, 119.1, 122.1, 124.0,
126.5, 126.7, 126.9, 127.7, 127.8, 128.0, 128.4, 128.5, 128.6, 128.8, 128.9, 129.1, 129.3,
129.4, 135.3, 137.7, 138.8, 141.3, 141.6, 142.1, 142.7, 147.6, 158.0, 159.5, 167.3,
168.3; HRMS calcd for C34H32NIO3 629.1427, found: 629.1426.
S5