Reaction Steps
Sodium tert-butoxide (0.4 g, 4 mmol) was added to a solution of 2-bromonaphthalene (0.3 g, 1.48 mmol) and 49 (0.4 g, 1.48 mmol) in 5 mL of anhydrous toluene at 25° C. Tris(dibenzylideneacetone)-dipalladium (0) (6 mg, 0.007 mmol) and (+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl [(±)-BINAP] (12.4 mg, 0.02 mmol) were added sequentially. The reaction mixture was heated to 80° C. and maintained at that temperature for 12 h, then was cooled to 25° C. and diluted with a mixture of CH3OH/CH2Cl2 (150 mL, v/v, 50:50). The diluted mixture was filtered through celite and the filtrate was concentrated in vacuo. The resulting residue was partitioned between CH2Cl2 (150 mL) and H2O (150 mL). The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to give a deep yellow solid residue. Purification of the residue by flash column chromatography (gradient elution 0 to 25% EtOAc in hexanes) provided the title compound (0.35 g, 59%): TLC (Rf =0.80; 40% EtOAc/hexanes); 1H NMR (CDCl3) δ 7.83 (d, 2H, J=8.4), 7.70 (m, 3H), 7.32 (m, 3H), 7.15 (d, 1H, J=2.1), 6.56 (d, 2H, J=8.7), 4.02 (d, 1H, J=7.8), 3.76 (d, 2H, J=12.7), 3.54 (m, 1H), 2.98 (t, 2H, J=12.0), 2.20 (d, 2H, J=10.7), 1.67 (m, 2H), 1.57 (s, 9H); 13C NMR (CDCl3) δ 166.0, 150.4, 149.1, 134.7, 131.5, 128.7, 128.5, 127.4, 126.7, 126.3, 123.4, 120.6, 119.8, 111.9, 110.7, 79.8, 49.6, 48.8, 32.1, 28.4; HRMS (FAB) m/z 402.2321 (M)+ (C26H30N2O2 requires 402.2307).
