2-Acetylnaphthalene → (S)-(-)-1-(2-Naphthyl)ethanol
Reaktionsgleichung
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([OH:13])[CH3:12].CC(C1C=CC2C(=CC=CC=2)C=1)=O.C1C2C(=CC=CC=2)C=CC=1[C@H](O)C>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C@@H:11]([OH:13])[CH3:12]Komponenten
4
Versuchsvorschrift
In Example 3, the biochemical conversion reaction of immobilized buckwheat protein for the substrate (±)-1-(2-naphthyl)ethanol (200 mg) required 4 days by going through bioconversion to 2-acetonaphthone accompanying sterically selective oxidation of (R)-1-(2-naphthyl)ethanol to obtain 100 mg of (S)-1-(2-naphthyl)ethanol at a yield of 50% and optical purity of 99% e.e. or higher. In Example 4, as a result of reacting with the substrate (±)-1-(2-naphthyl)ethanol by continuously recycling immobilized buckwheat protein used in this fourth step from the third step, optically active (S)-1-(2-naphthyl)ethanol was obtained at an optical purity of 99% e.e. or higher by going through a conversion mechanism which sterically selectively converts (R)-1-(2-naphthyl)ethanol to 2-acetonaphthone in the same manner as the first round. Continuous recycling of immobilized buckwheat protein maintained effectiveness for at least three rounds, and there were no changes observed in reaction time, chemical yield or optical purity.