Reaction Steps
In a nitrogen-filled glove box, a flame-dried 100-mL round-bottomed flask was charged with Sc(OTf)3 (0.38 g, 0.77 mmol, 3.0 equiv). The flask was capped with a rubber septum and removed from the glove box. Toluene (20 mL) was added and to the resulting suspension were added aniline 17 (0.35 g, 2.6 mmol, 10.0 equiv) and a toluene solution (1.5 mL) of epoxide 13 (0.20 g, 0.26 mmol, 1.0 equiv). The reaction was heated to 60° C. with vigorous stirring and maintained for 14 h. (Note: increased reaction times led to product decomposition), The reaction was cooled to rt, diluted with H2O (10 mL) and EtOAc (10 mL), and the resulting mixture was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with 0.5M HCl(aq.) (2×20 mL), saturated NaHCO3(aq.) (15 mL), dried with magnesium sulfate, and concentrated in vacuo. The crude product was purified via flash chromatography (90:10 to 80:20 hexanes:EtOAc) to afford anilino-alcohol 14 as a yellow, viscous oil (0.16 g, 66%) with recovery of the unreacted epoxide 13 (0.04 g, 18%). Analytical data: [α]D19 −39.3 (c=0.70, CHCl3); 1H NMR (600 MHz, CDCl3): δ 8.21 (d, J=6.6 Hz, 1H), 7.70 (d, J=6.6 Hz, 2H), 7.51 (d, J=7.2 Hz, 2H), 7.39 (t, J=7.2 Hz, 1H), 7.32 (t, J=7.2 Hz, 2H), 7.28-7.22 (m, 8H), 7.16 (t, J=7.2 Hz, 2H), 7.12 (t, J=7.8 Hz, 1H), 6.79 (d, J=7.8 Hz, 1H), 6.13 (s, 5.88 (s, 1H), 5.39-5.36 (m, 1H), 5.36 (s, 1H), 5.04 (d, J=12.0 Hz, 1H), 5.01 (d, J=12.0 Hz, 1H), 4.78 (dd, J=4.6, 6.6 Hz, 1H), 4.37 (d, J=10.2 Hz, 1H), 4.13 (s, 1H), 3.68 (dd, J=4.6, 3.0 Hz, 1H), 3.48 (d, J=10.8 Hz, 1H), 2.96 (s, 6H), 2.49 (s, 3H), 1.69 (s, 3H), 1.41 (d, J=6, 6 Hz, 3H), 0.98 (s, 9H), 0.92 (s, 9H), 0.12 (s, 3H), 0.02 (s, 3H); 13C NMR (150 MHz, CDCl3): δ 198.7, 158.6, 158.4, 149.5, 137.7, 136.6, 135.6, 135.4, 132.4, 132.0, 129.6, 128.8, 128.2, 128.1, 127.8, 127.6, 118.2, 117.0, 112.6, 83.6, 81.0, 70.3, 68.4, 66.9, 66.5, 63.0, 59.3, 36.6, 26.7, 26.7, 25.7, 21.2, 19.4, 19.0, 17.7, −4.3, −6.1; LRMS (ESI+) Calcd. for C50H70N8Si2+Na, 933.46. Found, 933.35. IR (thin film, cm−1) 3361, 2953, 2358, 1716, 1698, 1652, 1539, 1488, 1472, 1243, 1041, 829, 701; TLC (80:20 hexanes:EtOAc): Rf=0.35.
