C[C@H]1P(CCP2[C@H](C)CC[C@H]2C)[C@H](C)CC1.[CH3:17][O:18][C:19]1[CH:32]=[CH:31][C:22]2[C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:24][O:25][C:21]=2[CH:20]=1.[H][H]>CO>[CH3:17][O:18][C:19]1[CH:32]=[CH:31][C:22]2[CH:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH2:24][O:25][C:21]=2[CH:20]=1To a mixture of (1,5-cyclooctadiene)rhodium trifluoromethanesulfonate (12 mg) and (R,R)-Me-BPE (6.5 mg) was added methanol (2.5 mL) sufficiently substituted by argon gas, and the mixture was stirred at room temperature for 15 min. This was added to methyl (6-methoxy-1-benzofuran-3-yl)acetate (55 mg), and the mixture was stirred at 70° C. for 3 hr under 0.7 MPa hydrogen atmosphere. The reaction mixture was quantified by HPLC. As a result, the enantiomeric excess was 52.8%, and the yield was 24.3%.
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