A method for asymmetric catalytic synthesis of optically active 2-hydroxy-3,3-dimethyl-4-oxobutyrate
An oxobutyrate, optically active technology, applied in asymmetric synthesis, organic chemical methods, chemical instruments and methods, etc., can solve the problems of unsatisfactory asymmetric catalytic efficiency
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Embodiment 1
[0029] solvent effect
[0030] In a clean 5 mL round-bottomed flask equipped with a magnetic stirrer, add isobutyraldehyde (5 mmol, 0.46 mL), 0.25 mL of solvent, catalyst ( R )-Cat-1 (0.025 mmol, 5.6 mg) and acetic acid (0.025 mmol, 14.3 µL), stirred at room temperature for 10.0 min, then added ethyl glyoxylate (50% solution in toluene, 0.5 mmol, 1.0 mL), at room temperature The reaction was stirred under low pressure, and 20 mL of ethyl acetate was added after the reaction was detected by TLC, washed with a small amount of saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, prepared and purified by quick silica gel column chromatography with petroleum ether and ethyl acetate to obtain reaction product( R )-1a.
[0031] The influence of the solvent on the ee value of this asymmetric catalytic reaction is very significant, and the results are shown in Table 1 below.
[0032]
Embodiment 2
[0034] Effect of Additives on Enantioselectivity of Reaction
[0035] In a clean 5 mL round bottom flask equipped with a magnetic stirrer, add isobutyraldehyde (5 mmol, 0.46 mL), CH 2 Cl 2 (0.25 mL), catalyst ( R )-Cat-1 (0.025 mmol, 5.6 mg) and additives (0.025 mmol), stirred at rt for 10.0 min, then added ethyl glyoxylate (50% solution in toluene, 0.5 mmol, 1.0 mL), stirred at room temperature, After the reaction was detected by TLC, 20 mL of ethyl acetate was added, washed with a small amount of saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, prepared and purified by petroleum ether and ethyl acetate flash silica gel column chromatography to obtain the reaction product ( R )-1a.
[0036] The effects of various additives on the ee value of the asymmetrically catalyzed Aldol reaction are shown in Table 2 below.
[0037]
Embodiment 3
[0039] Enantioselectivity comparison of different catalysts.
[0040] In a clean 5 mL round bottom flask equipped with a magnetic stirrer, add isobutyraldehyde (5 mmol, 0.46 mL), CH 2 Cl 2 (0.25 mL), catalyst ( R )-Cat (0.025 mmol) and acetic acid (0.025 mmol, 14.3 µL), stirred at room temperature for 10.0 min, then added ethyl glyoxylate (50% solution in toluene, 0.5 mmol, 1.0 mL), stirred at room temperature, and detected by TLC After the reaction was completed, 20 mL of ethyl acetate was added, washed with a small amount of saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, prepared and purified by petroleum ether and ethyl acetate flash silica gel column chromatography to obtain the reaction product ( R )-1a.
[0041] The enantioselective catalytic effects of the three catalysts are shown in Table 3 below, and the results show that the catalyst ( R )-Cat-1 had the highest enantioselectivity.
[0042]
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