C[C@H]1P(CCP2[C@H](C)CC[C@H]2C)[C@H](C)CC1.[OH:17][C:18]1[CH:31]=[CH:30][C:21]2[C:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:23][O:24][C:20]=2[CH:19]=1.[H][H]>CO>[OH:17][C:18]1[CH:31]=[CH:30][C:21]2[CH:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:23][O:24][C:20]=2[CH:19]=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 with argon gas, and the mixture was stirred at room temperature for 15 min. This was added to methyl (6-hydroxy-1-benzofuran-3-yl)acetate (51 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 47.9%, and the yield was 41.5%.
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