Reaction Steps
The general procedure C using 23 (56.8 mg, 0.077 mmol), N-methylaniline (10 μL, 0.092 mmol), Pd(OAc)2 (0.7 mg, 0.003 mmol), (o-biphenyl)P(t-Bu)2 (1.8 mg, 0.006 mmol) and NaOtBu (10.4 mg, 0.11 mmol) for 12 h at room temperature afforded a yellow oil. Cleavage of the aminated intermediate with SnCl4 (92 μL 1.0 M in CH2Cl2, 0.092 mmol) using general procedure D gave 38.0 mg (81%) of 29 as a colorless oil after purification by flash column chromatography on silica gel (25% EtOAc/Hexanes). [α]24 D: −13.6° (c 6.02, CH2Cl2); IR (thin film) 3456, 3070, 2930, 1113, 1055 cm−1; 1H-NMR (CDCl3) δ 7.89 (dd, J=0.6, 6.7 Hz, 2H), 7.83 (dd, J=0.9, 6.7 Hz, 2H), 7.54-7.33 (m, 16H), 5.07 (d, J=11.3 Hz, 1H), 5.04 (d, J=11.0 Hz, 1H), 5.01 (d, J=11.0 Hz, 1H), 4.84 (d, J=11.0 Hz, 1H), 4.32 (d, J=7.6 Hz, 1H), 4.10-4.04 (m, 2 H), 3.91 (dd, J=9.2, 9.2 Hz, 1H), 3.76-3.67 (m, 5H), 3.51-3.46 (m, 1H), 2.83 (br s, 1H), 1.18 (s, 9H); 13 C-NMR (CDCl3) δ 138.9, 138.4, 136.2, 135.8, 133.9, 133.3, 129.9, 128.8, 128.7, 128.3, 128.2, 128.0, 127.8, 103.8, 84.8, 77.7, 76.2, 75.6, 75.4, 75.0, 62.9, 56.9, 27.0, 19.6; FAB MS m/z (M+Na)+: calcd 635.2805, obsd 635.2804.
