Chiral ferrocene sulfonic acid catalyst as well as preparation method and application thereof
A ferrocene sulfonic acid and a catalyst technology are applied in the field of a chiral ferrocene sulfonic acid catalyst and its preparation, and achieve the effects of simple preparation, novel catalyst structure and mild reaction conditions
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[0039] The present invention also provides a preparation method of the above-mentioned chiral ferrocenesulfonic acid catalyst, comprising the following steps:
[0040] The present invention also provides a preparation method of the above-mentioned chiral ferrocenesulfonic acid catalyst, comprising the following steps:
[0041] (1) R-N,N-dimethylferrocene ethylamine, anhydrous n-hexane, tert-butyllithium solution, p-toluenesulfonyl azide are mixed and reacted, and the azide ferrocene amine is obtained after extraction and concentration derivative 1;
[0042] (2) After mixing the azide ferrocene derivative 1, anhydrous ethanol and Pd / C, a reduction reaction is carried out under a hydrogen atmosphere, and the ferrocene whose azide is reduced to an amino group is obtained after filtration and concentration Amine derivative 2;
[0043] (3) ferrocene amine derivative 2, anhydrous dichloromethane, R-isothiocyanate are mixed and reacted, concentrated and crossed the column to obtain...
Embodiment 1
[0063] In a 100mL double-necked round-bottom flask, add 2 mmol of R-N,N-dimethylferroceneethylamine, add 20 mL of anhydrous n-hexane, lower the reaction temperature to -78°C, and slowly add 2.5 mmol to a concentration of 1.6 mol / L tertiary The butyllithium solution was added with 2.2 mmol of p-toluenesulfonyl azide after the reaction for 30 min, and the reaction was continued for 1 h. After the reaction was completed, saturated brine was added to terminate the reaction, extracted with ethyl acetate, and concentrated to obtain the ferricocene azide derivative. Compound 1; the product was directly added to 20 mL of anhydrous ethanol, and then 10 mg of Pd / C (10%) was added, and the reaction flask was filled with a hydrogen balloon (the rate of hydrogen gas inflow), reacted at 60 °C for 10 h, and filtered directly after the reaction. After the filtrate was concentrated, the ferrocene derivative 2 in which azide was reduced to amino group was obtained; this derivative was added to 1...
Embodiment 2
[0070] Catalyst A2 preparation process is with embodiment 1, and the difference is that the structural formula of R-isothiocyanate is:
[0071]
[0072] 50mg N,N-dimethylaniline, 45mg N-(1-styryl)-acetamide were added to a 10mL single-neck reaction flask, 3mL of n-hexane was added to dissolve, then 5mg of catalyst A2 was added, and the reaction was carried out at room temperature for 16h. Pass the column directly to obtain a white solid product with a yield of 79% and an ee value of 81%.
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