(S)-3-羟基-3-苯基丙酸乙酯

反应条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of Example 45 shown in Table 9 (14 mg, 0.05 mmol) was added to titanium tetrachloride (9.5 mg, 0.05 mmol) in toluene (1.0 ml), and the resultant mixture was stirred until the mixture became uniform. After titanium was coordinated with the compound, the solvent was removed through evaporation under reduced pressure at room temperature. The resultant residue was dissolved in anhydrous tetrahydrofliran (10 ml), and the solution was cooled to −20° C. Separately, benzaldehyde (106 mg, 1.0 mmol) and 1-ethoxy-1-trimethylsiloxyethene (192 mg, 1.2 mmol) were dissolved in anhydrous tetrahydrofuran (2 ml), and the resultant solution was added to the above solution, and then the resultant mixture was stirred at −20° C. for one day. Tetrahydrofuran (2 ml) containing trifluoroacetic acid in an amount of 10 w/w% was added to the resultant reaction mixture, and the mixture was returned to room temperature. The reaction mixture was diluted with water, and then subjected to extraction with ether. The organic layer was washed with salt water, and dried over anhydrous magnesium sulfate. After removal of the solvent, the resultant oily product was purified through silica gel chromatography, to thereby yield colorless oily ethyl (S)-3-hydroxy-3-phenylpropionate ([α]D20-25.5 (cl, CHCl3)) at a yield of 70%. the solvent was removed through evaporation under reduced pressure at room temperature The resultant residue was dissolved in anhydrous tetrahydrofliran (10 ml) w/w% was added to the resultant reaction mixture was returned to room temperature subjected to extraction with ether The organic layer was washed with salt water dried over anhydrous magnesium sulfate After removal of the solvent the resultant oily product was purified through silica gel chromatography

反应条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of Example 45 shown in Table 9 (14 mg, 0.05 mmol) was added to titanium tetrachloride (9.5 mg, 0.05 mmol) in toluene (1.0 ml), and the resultant mixture was stirred until the mixture became uniform. After titanium was coordinated with the compound, the solvent was removed through evaporation under reduced pressure at room temperature. The resultant residue was dissolved in anhydrous tetrahydrofliran (10 ml), and the solution was cooled to −20° C. Separately, benzaldehyde (106 mg, 1.0 mmol) and 1-ethoxy-1-trimethylsiloxyethene (192 mg, 1.2 mmol) were dissolved in anhydrous tetrahydrofuran (2 ml), and the resultant solution was added to the above solution, and then the resultant mixture was stirred at −20° C. for one day. Tetrahydrofuran (2 ml) containing trifluoroacetic acid in an amount of 10 w/w% was added to the resultant reaction mixture, and the mixture was returned to room temperature. The reaction mixture was diluted with water, and then subjected to extraction with ether. The organic layer was washed with salt water, and dried over anhydrous magnesium sulfate. After removal of the solvent, the resultant oily product was purified through silica gel chromatography, to thereby yield colorless oily ethyl (S)-3-hydroxy-3-phenylpropionate ([α]D20-25.5 (cl, CHCl3)) at a yield of 70%. the solvent was removed through evaporation under reduced pressure at room temperature The resultant residue was dissolved in anhydrous tetrahydrofliran (10 ml) w/w% was added to the resultant reaction mixture was returned to room temperature subjected to extraction with ether The organic layer was washed with salt water dried over anhydrous magnesium sulfate After removal of the solvent the resultant oily product was purified through silica gel chromatography

反应条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of Example 45 shown in Table 9 (14 mg, 0.05 mmol) was added to titanium tetrachloride (9.5 mg, 0.05 mmol) in toluene (1.0 ml), and the resultant mixture was stirred until the mixture became uniform. After titanium was coordinated with the compound, the solvent was removed through evaporation under reduced pressure at room temperature. The resultant residue was dissolved in anhydrous tetrahydrofliran (10 ml), and the solution was cooled to −20° C. Separately, benzaldehyde (106 mg, 1.0 mmol) and 1-ethoxy-1-trimethylsiloxyethene (192 mg, 1.2 mmol) were dissolved in anhydrous tetrahydrofuran (2 ml), and the resultant solution was added to the above solution, and then the resultant mixture was stirred at −20° C. for one day. Tetrahydrofuran (2 ml) containing trifluoroacetic acid in an amount of 10 w/w% was added to the resultant reaction mixture, and the mixture was returned to room temperature. The reaction mixture was diluted with water, and then subjected to extraction with ether. The organic layer was washed with salt water, and dried over anhydrous magnesium sulfate. After removal of the solvent, the resultant oily product was purified through silica gel chromatography, to thereby yield colorless oily ethyl (S)-3-hydroxy-3-phenylpropionate ([α]D20-25.5 (cl, CHCl3)) at a yield of 70%. the solvent was removed through evaporation under reduced pressure at room temperature The resultant residue was dissolved in anhydrous tetrahydrofliran (10 ml) w/w% was added to the resultant reaction mixture was returned to room temperature subjected to extraction with ether The organic layer was washed with salt water dried over anhydrous magnesium sulfate After removal of the solvent the resultant oily product was purified through silica gel chromatography

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In 0.5 ml of dried and degassed DMF were dissolved 4.9 mg (15 μmol) of (R,R)-t-Bu-QuinoxP*(1) and 3.4 mg (6.7 μmol) of [RuCl2(η6-C6H6)]2 in a nitrogen atmosphere. The mixture was heated at 100° C. for 10 minutes. After cooling to 50° C., the solvent was removed by evaporation under reduced pressure to give a catalyst as a reddish to purple solid. The resulting catalyst was dissolved in 3 ml of degassed ethanol in a glove box. To the solution was added a solution of 129 mg (0.67 mmol) of ethyl 3-oxo-3-phenylpropionate in 1 ml of dichloromethane, and the mixture was transferred into a stainless steel autoclave. After purging the autoclave with hydrogen four times, hydrogen was introduced into the autoclave to 20 atm. The reaction mixture in the autoclave was stirred at 50° C. for 24 hours. After cooling to room temperature, hydrogen gas was released from the autoclave. The solvent was removed, and the residue was dissolved in diethyl ether. The resulting solution was washed successively with water and a sodium chloride aqueous solution, and the organic layer was dried over anhydrous sodium sulfate. Any volatile matter was removed by evaporation, and the residue was purified by silica gel column chromatography to give the title compound, ethyl (S)-3-hydroxy-3-phenylpropionate. In 0.5 ml of dried degassed DMF After cooling to 50° C. the solvent was removed by evaporation under reduced pressure to give a catalyst as a reddish to purple solid After purging the autoclave with hydrogen four times, hydrogen was introduced into the autoclave to 20 atm After cooling to room temperature The solvent was removed the residue was dissolved in diethyl ether The resulting solution was washed successively with water a sodium chloride aqueous solution, and the organic layer was dried over anhydrous sodium sulfate Any volatile matter was removed by evaporation the residue was purified by silica gel column chromatography

反应条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound of Example 45 shown in Table 9 (14 mg, 0.05 mmol) was added to titanium tetrachloride (9.5 mg, 0.05 mmol) in toluene (1.0 ml), and the resultant mixture was stirred until the mixture became uniform. After titanium was coordinated with the compound, the solvent was removed through evaporation under reduced pressure at room temperature. The resultant residue was dissolved in anhydrous tetrahydrofliran (10 ml), and the solution was cooled to −20° C. Separately, benzaldehyde (106 mg, 1.0 mmol) and 1-ethoxy-1-trimethylsiloxyethene (192 mg, 1.2 mmol) were dissolved in anhydrous tetrahydrofuran (2 ml), and the resultant solution was added to the above solution, and then the resultant mixture was stirred at −20° C. for one day. Tetrahydrofuran (2 ml) containing trifluoroacetic acid in an amount of 10 w/w% was added to the resultant reaction mixture, and the mixture was returned to room temperature. The reaction mixture was diluted with water, and then subjected to extraction with ether. The organic layer was washed with salt water, and dried over anhydrous magnesium sulfate. After removal of the solvent, the resultant oily product was purified through silica gel chromatography, to thereby yield colorless oily ethyl (S)-3-hydroxy-3-phenylpropionate ([α]D20-25.5 (cl, CHCl3)) at a yield of 70%. the solvent was removed through evaporation under reduced pressure at room temperature The resultant residue was dissolved in anhydrous tetrahydrofliran (10 ml) w/w% was added to the resultant reaction mixture was returned to room temperature subjected to extraction with ether The organic layer was washed with salt water dried over anhydrous magnesium sulfate After removal of the solvent the resultant oily product was purified through silica gel chromatography