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detector at 254 nm).
IR (thin film): ν 2953, 1741, 1708, 1648, 1258 cm -1 .
270e (major diastereomer, Rt = 17 min, HPLC, hexanes-EtOAc, 6 : 1 v/v): 1 H NMR (300 MHz,
CDCl3): δ 7.49-7.43 (m, 5H), 5.56 (s, 1H), 4.75 (d, J = 17.1 Hz, 1H), 4.74 (d, J = 10.4 Hz, 1H),
4.45 (d, J = 17.4 Hz, 1H), 4.15 (d, J = 10.3 Hz, 1H), 3.74 (s, 3H), 2.89 (q, J = 7.5 Hz, 1H), 1.65
(s, 3H), 1.28 (d, J = 7.5 Hz, 3H), 0.81 (s, 9H), 0.07 (s, 3H), 0.02 (s, 3H); 13 C NMR (75 MHz,
CDCl3): δ 206.5, 171.7, 170.5, 154.3, 144.3, 141.3, 135.9, 134.3, 130.0, 128.8, 126.5, 118.8,
66.1, 65.3, 52.6, 45.6, 41.9, 25.7, 18.0, 13.6, 7.9, -5.4, -5.6; MS m/z (%) 469 (37), 439 (30), 412
(30), 324 (20), 105 (100); EI-HRMS calcd for C26H35NO5Si m/z [M] + 469.2285; found 469.2280.
270e (minor diastereomer, Rt = 26 min, HPLC, hexanes-EtOAc, 6 : 1 v/v): 1 H NMR (300 MHz,
CDCl3): δ 7.50-7.42 (m, 5H), 5.59 (s, 1H), 4.74 (d, J = 18.0 Hz, 1H), 4.72 (d, J = 10.2 Hz, 1H),
4.47 (1d, J = 17.8 Hz, 1H), 4.15 (d, J = 10.3 Hz, 1H), 3.75 (s, 3H), 2.91 (q, J = 7.6 Hz, 1H), 1.64
(s, 3H), 1.27 (d, J = 7.6 Hz, 9H), 0.80 (s, 3H), 0.07 (s, 3H), 0.02 (s, 3H); 13 C NMR (75 MHz,
CDCl3): δ 206.6, 171.9, 170.4, 154.6, 141.2, 135.9, 134.2, 130.0, 128.9, 126.5, 118.8, 65.9, 65.1,
52.6, 45.9, 41.6, 25.6, 17.9, 14.2, 7.9, -5.5, -5.7; MS m/z (%) 469 (7), 439 (30), 412 (35), 324
(22), 105 (100); EI-HRMS calcd for C26H35NO5Si m/z [M] + 469.2285; found 469.2299.
Cbz
MeO 2C
N
3,5,7-Trimethyl-6-oxo-1,3,5,6-tetrahydro-[2]pyrindine-2,3-dicarboxylic acid 2-benzyl ester
3-methyl ester (270f). Prepared by following general procedure N, using: 73f (25 mg, 73 µmol),
[Rh(CO)2Cl]2 (3 mg, 8 µmol), PPh3 (5 mg, 20 µmol), AgBF4 (150 µL of 0.1 M solution in DCE,
15 µmol). The reaction was stirred at rt for 1 h. Yield 270f (19 mg, 75%).
1 H NMR (300 MHz, DMSO-d6): δ 7.41-7.30 (m, 5H), 5.72 (s, 1H), 5.15 (s, 2H), 4.86 (d, J =
270f
240
O