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1 H NMR (300 MHz, CDCl3): δ 7.68-7.64 (m, 2H), 7.46-7.38 (m, 3H), 7.33-7.21 (m, 5H), 5.83-
5.80 (m, 1H), 5.57-5.41 (m, 1H), 3.98-3.91 (m, 1H), 3.76 (s, 1.9H), 3.75 (s, 1.1H), 3.67-3.65 (m,
1H), 3.52-3.41 (m, 2H), 1.81 (dd, J = 7.2, 3.1 Hz, 1.9H), 1.77 (dd, J = 7.1, 3.1 Hz, 1.1H), 0.16 (s,
5.7H), 0.15 (s, 3.3H); 13 C NMR (75 MHz, CDCl3): δ 204.6, 172.6, 171.5, 136.4, 136.3, 135.8,
130.9, 130.3, 128.2, 128.0, 127.3, 126.8, 103.2, 90.9, 90.4, 89.4, 68.8, 52.4, 39.8, 38.8, 38.5,
13.9, 13.7, -0.3; IR (thin film): ν 2952, 2177, 1967, 1745, 1649 cm -1 ; MS m/z (%) 445 (21), 444
(36), 354 (50), 244 (74), 105 (100); EI-HRMS calcd for C27H30NO3Si m/z [M-1] + 444.1995;
found 444.1984.
BzN
MeO 2C
Bn
73d
2-[Benzoyl(3-phenylprop-2-ynyl)amino]-2-benzylhexa-3,4-dienoic acid methyl ester (73d).
Prepared by following general procedure F, using: 58a (72 mg, 0.21 mmol), NaH (17 mg of 60%
dispersion in mineral oil, 0.43 mmol), (3-bromoprop-1-ynyl)-benzene (66 mg, 0.34 mmol).
Purification by flash chromatography (hexanes-EtOAc, 9 : 1, v/v) afforded 73d (86 mg, 89%) as
a mixture of diastereomers in a ~1.6 : 1 ratio determined by integration of the methyl group
resonances in the 1 H NMR.
1 H NMR (300 MHz, CDCl3): δ 7.79-7.77 (m, 2H), 7.57-7.51 (m, 4H), 7.41-7.23 (m, 9H), 5.98
(sept, J = 3.1 Hz, 1H), 5.65-5.50 (m, 1H), 4.11 (d, J = 13.6 Hz, 0.61H), 4.11-4.01 (m, 2H), 3.87
(s, 1.2H), 3.85 (s, 1.8H), 3.83-3.77 (m, 1H), 3.54 (d, J = 13.5 Hz, 1H), 1.89 (dd, J = 7.2, 3.2 Hz,
1.8H), 1.83 (dd, J = 7.1, 3.2 Hz, 1.2H); 13 C NMR (75 MHz, CDCl3): δ 204.6, 172.7, 172.6,
171.7, 171.6, 136.4, 136.3, 131.6, 131.5, 131.0, 130.4, 128.4, 128.3, 128.2, 128.0, 127.3, 126.9,
122.6, 90.9, 90.8, 90.4, 86.4, 86.3, 84.2, 69.0, 68.9, 52.4, 39.8, 39.0, 38.7, 13.9, 13.7; IR (thin
film): ν 2948, 1967, 1743, 1645, 1392 cm -1 ; MS m/z (%) 448 (7), 390 (78), 358 (25), 105 (100);
170
•
Ph
H