Reaction Steps
The general procedure C using 20 (73.1 mg, 0.135 mmol), morpholine (14.1 μL, 0.162 mmol), Pd(OAc)2 (1.2 mg, 0.0054 mmol), 1-(N,N-dimethylamino)-1′-(dicyclohexylphosphino) biphenyl (5.4 mg, 0.0054 mmol) and K3PO4 (40.0 mg, 0.189 mmol) for 12 h at 100° C. afforded a yellow oil. Cleavage of the aminated intermediate with SnCl4 (162 μL 1.0 M in CH2Cl2, 0.162 mmol) using general procedure D gave 49.0 mg (87%) of 26 as a white solid after purification by flash column chromatography on silica gel (50% EtOAc/Hexanes). [α]D: −23.5° (c 3.24, CH2Cl2); IR (thin film) 3474, 2879, 1747, 1234, 1082 cm−1; 1H-NMR (CDCl3) δ 7.37–7.26 (m, 10H), 5.00–4.92 (m, 1H), 4.85 (d, J=11.0 Hz, 1H), 4.83 (d, J=11.9 Hz, 1H), 4.69 (d, J=11.0 Hz, 1H), 4.67 (d, J=11.0 Hz, 1H), 4.34 (d, J=7.9 Hz, 1H), 3.92–3.88 (m, 1H), 3.77–3.69 (m, 3H), 3.49 (s, 3H), 3.42–3.40 (m, 1H), 1.98 (s, 3H); 13C-NMR (CDCl3) δ 169.8, 138.2, 137.9, 128.7, 128.6, 128.2, 128.1, 128.0, 127.9, 102.1, 82.7, 77.7, 75.4, 75.3, 75.2, 73.2, 61.9, 57.1, 21.1; FAB MS m/z (M+Na)+: calcd 439.1733, obsd 439.1730.
