(1R)-1-(4-bromophenyl)ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As shown here, the biochemical conversion reaction of immobilized buckwheat protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 11 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (S)-1-(4-bromophenyl)ethanol to obtain 114 mg of (R)-1-(4-bromophenyl)ethanol at a yield of 57%. Optical purity was obtained at 88% e.e.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As shown here, the biochemical conversion reaction of immobilized soy bean protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 2 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (S)-1-(4-bromophenyl)ethanol to obtain 108 mg of (R)-1-(4-bromophenyl)ethanol at a yield of 54%. Optical purity was obtained at 88% e.e. Equipment conditions were the same as for immobilized green pea protein.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As shown here, the biochemical conversion reaction of immobilized green pea protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 8 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (R)-1-(4-bromophenyl)ethanol to obtain 114 mg of (S)-1-(4-bromophenyl)ethanol at a yield of 57%. Optical purity was obtained at 88% e.e. The reaction course and time at completion of reaction were determined by GC using the Hitachi Model G-3500 gas chromatograph under conditions consisting of carrier gas: He at 0.48 ml/min, split ratio: 1/55, oven temperature: 150° C., inlet temperature: 250° C., outlet temperature: 250° C., pressure: 136, flow rate value: 42, analytical column: TC-5HT 0.25 mm I.D.×30M df (GL Science).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As shown here, the biochemical conversion reaction of immobilized buckwheat protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 11 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (S)-1-(4-bromophenyl)ethanol to obtain 114 mg of (R)-1-(4-bromophenyl)ethanol at a yield of 57%. Optical purity was obtained at 88% e.e.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As shown here, the biochemical conversion reaction of immobilized buckwheat protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 11 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (S)-1-(4-bromophenyl)ethanol to obtain 114 mg of (R)-1-(4-bromophenyl)ethanol at a yield of 57%. Optical purity was obtained at 88% e.e.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As shown here, the biochemical conversion reaction of immobilized soy bean protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 2 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (S)-1-(4-bromophenyl)ethanol to obtain 108 mg of (R)-1-(4-bromophenyl)ethanol at a yield of 54%. Optical purity was obtained at 88% e.e. Equipment conditions were the same as for immobilized green pea protein.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As shown here, the biochemical conversion reaction of immobilized soy bean protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 2 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (S)-1-(4-bromophenyl)ethanol to obtain 108 mg of (R)-1-(4-bromophenyl)ethanol at a yield of 54%. Optical purity was obtained at 88% e.e. Equipment conditions were the same as for immobilized green pea protein.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As shown here, the biochemical conversion reaction of immobilized green pea protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 8 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (R)-1-(4-bromophenyl)ethanol to obtain 114 mg of (S)-1-(4-bromophenyl)ethanol at a yield of 57%. Optical purity was obtained at 88% e.e. The reaction course and time at completion of reaction were determined by GC using the Hitachi Model G-3500 gas chromatograph under conditions consisting of carrier gas: He at 0.48 ml/min, split ratio: 1/55, oven temperature: 150° C., inlet temperature: 250° C., outlet temperature: 250° C., pressure: 136, flow rate value: 42, analytical column: TC-5HT 0.25 mm I.D.×30M df (GL Science).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As shown here, the biochemical conversion reaction of immobilized green pea protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 8 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (R)-1-(4-bromophenyl)ethanol to obtain 114 mg of (S)-1-(4-bromophenyl)ethanol at a yield of 57%. Optical purity was obtained at 88% e.e. The reaction course and time at completion of reaction were determined by GC using the Hitachi Model G-3500 gas chromatograph under conditions consisting of carrier gas: He at 0.48 ml/min, split ratio: 1/55, oven temperature: 150° C., inlet temperature: 250° C., outlet temperature: 250° C., pressure: 136, flow rate value: 42, analytical column: TC-5HT 0.25 mm I.D.×30M df (GL Science).

反応条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-(4-bromophenyl)ethanone (5.0 g, 25 mmol) and (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole (1.25 mL, 1 M) in 80 mL of anhydrous dichloromethane was added Borane-methyl sulfide complex (2.1 g, 27 mmol) over 1 hour at −200C. After addition completed, the mixture was stirred at −20° C. for 2 hours, then stirred at room temperature for 12 hours. After the reaction, 20 mL of methanol was added, and stirred for 0.5 hour. Then the mixture was diluted with 100 mL of water and the organic phase was collected, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1) to give (R)-1-(4-bromophenyl)ethanol (4.6 g, 92%) as the white solid. After addition stirred at room temperature for 12 hours was added stirred for 0.5 hour the organic phase was collected dried over anhydrous sodium sulfate concentrated purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=20:1)

反応条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-bromoacetophenone (5.0 g, 25 mmol) and (S)-2-Methyl-CBS-oxazaborolidine (1.25 mL, 1 M) in anhydrous dichloromethane (80 mL) was added borane-methyl sulfide complex (2.1 g, 27 mmol) over 1 hour at −20° C. After addition completed, the mixture was stirred at −20° C. for 2 hours, then stirred at room temperature for 12 hours. After the reaction, methanol (20 mL) was added, and stirred for 0.5 hour. Then the mixture was diluted with water (100 mL) and the organic phase was dried over anhydrous sodium sulfate. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:8) to give pure product (R)-1-(4-bromophenyl)ethanol as a white solid (4.6 g, 92%). After addition stirred at room temperature for 12 hours was added stirred for 0.5 hour the organic phase was dried over anhydrous sodium sulfate The mixture was filtered the filtrate was concentrated The residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:8)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: As shown here, the biochemical conversion reaction of immobilized buckwheat protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 11 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (S)-1-(4-bromophenyl)ethanol to obtain 114 mg of (R)-1-(4-bromophenyl)ethanol at a yield of 57%. Optical purity was obtained at 88% e.e.