Triphenylphosphine → 3-(3-Fluoro-phenyl)-2-(2-oxoethyl)-pentanedioic acid 1-methyl ester
反応式
[CH3:1][O:2][C:3](=[O:20])[CH:4]([CH2:17][CH:18]=C)[CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8].[O:21]=[O+][O-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[CH:4]([CH2:17][CH:18]=[O:21])[CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8]参加物
5
実験手順
A mixture of 2-allyl-3-(3-fluoro-phenyl)-pentanedioic acid 1-methyl ester (2-5) (1.01 g, 3.28 mmol) and Sudan Red B (0.01 g) in 100 mL CH2Cl2 was treated with ozone at -78° C. for 20 min. Then excess ozone was purged with argon, followed with the addition of PPh3 (2.00 g, 7.63 mmol). The mixture was stirred for 30 min and concentrated under diminished pressure. The residue was purified by flash silica chromatography (EtOAc/Hexane, 1:3) to provide the desired product as two separated pairs of enantiomers (2-6A and 2-6B).