A kind of silicon stereocenter chiral compound and its synthesis method
A technology of chiral compounds and synthesis methods, applied in the field of chemical synthesis, can solve the problems of low chemoselectivity and stereoselectivity, poor substrate applicability, etc., and achieve simple and easy preparation methods, convenient post-processing, and good adaptability Effect
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preparation example 1
[0030] Preparation Example 1: Synthesis of tert-butyldiphenylpyridinesilane
[0031] Add 2-bromopyridine (15.8g, 100mmol), N,N,N',N'-tetramethylethylenediamine (23.2g, 200mmol) and 100mL of anhydrous diethyl ether into a 500mL Shlenk bottle, cool to -78°C 2.5M n-butyllithium-n-hexane solution (40ml, 100mmol) was added dropwise under nitrogen protection, stirred at this temperature for 1 hour, and then tert-butyldiphenylsilane (26mL, 100mmol) was added. After stirring at -78°C for 30 minutes, the temperature was raised naturally and reacted overnight. After the reaction was completed, it was quenched with water, extracted with petroleum ether, washed with brine, concentrated, the mixture was concentrated under reduced pressure after flash column chromatography, and the solid was washed with a small amount of methanol to obtain 12.7 g of white solid with a yield of 40%.
[0032] 1 H NMR (400MHz, CDCl 3 )δ8.89(d, J=4.3Hz, 1H), 7.67(d, J=6.6Hz, 4H), 7.50(td, J=7.6, 1.5Hz, 1H), ...
preparation example 2
[0035] Preparation Example 2: Synthesis of tert-butyldiphenylquinolinesilane
[0036] Add 2-bromoquinoline (20.8g, 100mmol), N,N,N',N'-tetramethylethylenediamine (23.2g, 200mmol) and 100mL of anhydrous ether into a 500mL Shlenk bottle, cool to -78 °C, 2.5M n-butyllithium-n-hexane solution (40 mL, 100 mmol) was added dropwise under nitrogen protection, stirred at this temperature for 1 hour, and then tert-butyldiphenylsilane (26 mL, 100 mmol) was added. After stirring at -78°C for 30 minutes, the temperature was raised naturally and reacted overnight. After the reaction was completed, it was quenched with water, extracted with petroleum ether, washed with brine, concentrated, the mixture was concentrated under reduced pressure after flash column chromatography, and the solid was washed with a small amount of methanol to obtain 13.9 g of a white solid with a yield of 38%.
[0037] 1 H NMR (400MHz, CDCl 3 )δ8.44(d, J=8.4Hz, 1H), 8.04(d, J=8.3Hz, 1H), 7.94(d, J=6.4Hz, 4H), 7.85...
Embodiment 1
[0040] Embodiment 1: (S, E)-3-(2-(tert-butyl (phenyl) (pyridin-2-yl) silyl) phenyl) methyl acrylate synthesis
[0041] To a 50mL Shlenk bottle was added tert-butyldiphenylpyridinesilane (317mg, 1mmol), palladium acetate (0.1mmol, 22.4mg), anhydrous copper acetate (136.2mg, 0.2mmo), Fmoc-Phe-OH (77.5mg , 0.2mmol) and methyl acrylate (0.27mL, 3.0mmol), 5mL of isopropanol was added under an atmosphere of oxygen, stirred at room temperature for 30 minutes, and then stirred at 80°C for 48 hours. After flash column chromatography and concentration under reduced pressure, 108 mg of white solid was obtained with a yield of 27%.
[0042] 1 H NMR (400MHz, CDCl 3 )δ8.79(d, J=4.6Hz, 1H), 7.96(d, J=7.2Hz, 1H), 7.66(d, J=6.6Hz, 2H), 7.52(d, J=7.6Hz, 1H) , 7.47(d, J=15.7Hz, 1H), 7.32(dddd, J=32.9, 25.6, 13.3, 4.4Hz, 7H), 7.11(dd, J=6.9, 5.5Hz, 1H), 5.92(d, J =15.7Hz, 1H), 3.44(s, 3H), 1.14(s, 9H).
[0043] 13 C NMR (101MHz, CDCl 3 )δ 166.76, 164.77, 149.83, 147.27, 141.41, 137.93, 136...
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