CC1C=C2C(N=CC=C2)=C2C=1C=CC=N2.C([O-])([O-])=O.[Cs+].[Cs+].I[C:23]1[CH:24]=[C:25]([O:29][CH3:30])[CH:26]=[CH:27][CH:28]=1.[C:31]1([C@H:37]([OH:39])[CH3:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>[Cu]I.C1(C)C=CC=CC=1>[C:31]1([C@H:37]([O:39][C:23]2[CH:24]=[C:25]([O:29][CH3:30])[CH:26]=[CH:27][CH:28]=2)[CH3:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1A test tube was charged with CuI (20 mg, 0.10 mmol, 10 mol %), 5-methyl-1,10-phenanthroline (39 mg, 0.20 mmol, 20 mol %), Cs2CO3 (652 mg, 2.0 mmol), 3-iodoanisole (119 μL, 1.0 mmol), (R)-(+)-1-phenylethanol (205 μL, 1.7 mmol, >99% ee) and toluene (1 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 32 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane/ethyl acetate 30:1) provided 173 mg (76% yield, 98% ee) of the title compound as a colorless oil.
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