Chiral tetraaryl-substituted methane and its preparation method
A chiral and aryl technology, applied in the field of chiral tetraaryl substituted methane and its preparation, can solve the problems of limited types and synthesis of aryl methane, and achieve the effects of good yield, environmental friendliness, simple and practical operation
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[0023] On the other hand, the embodiment of the present invention also provides a preparation method of chiral tetraaryl-substituted methane, comprising the following steps:
[0024] dissolving the compound represented by formula II and the compound represented by formula III in a solvent, and performing a synthesis reaction under the condition of a chiral phosphoric acid catalyst to obtain the compound represented by formula I;
[0025]
[0026] Among them, in the above compounds, Ar 1 、Ar 2 、Ar 3 and Ar 4 are independently selected from any one of aryl, heteroaryl, substituted aryl and substituted heteroaryl, and Ar 1 、Ar 2 、Ar 3 and Ar 4 different from each other.
[0027] In the above-mentioned preparation method provided by the embodiment of the present invention, the compound shown in formula II, that is, triaryl-substituted methanol and the compound shown in formula III, that is, aryl nucleophile are used to react under the condition of chiral phosphoric acid ...
Embodiment 1
[0039]
[0040] Using Ar 1 For 4-hydroxyphenyl, Ar 2 is 2-methoxyphenyl, Ar 3 The phenyl triaryl carbinol and 2-methylpyrrole are used as reaction raw materials, and the reaction is carried out with a chiral phosphoric acid catalyst. The specific implementation process is as follows:
[0041] Dissolve triarylmethanol (61.2mg, 0.2mmol) and 2-methylpyrrole (32.4mg, 0.4mmol) in 1,2-dichloroethane (3.6mL), and cool the mixture to 0°C, slowly drop A solution of chiral phosphoric acid (14.9 mg, 0.015 mmol) in 1,2-dichloroethane (0.4 mL) was added. After that, it was placed at 0°C and stirred for 48 hours. Its reaction equation is as follows:
[0042]
[0043] The reaction solution was directly applied to silica gel column chromatography to obtain 71.7 mg of the target product Ia as a pale yellow foamy solid, with a calculated yield of 97%.
[0044] After the preparation of this step is completed, in order to further verify that the purified compound is indeed the target ...
Embodiment 2
[0053]
[0054] Using Ar 1 For 4-hydroxyphenyl, Ar 2 For 2-benzo[1,3]-dioxolanyl, Ar 3 The phenyl triaryl carbinol and 2-methylpyrrole are used as reaction raw materials, and the reaction is carried out with a chiral phosphoric acid catalyst. The specific implementation process is as follows:
[0055] Dissolve triarylmethanol (64.0mg, 0.2mmol) and 2-methylpyrrole (32.4mg, 0.4mmol) in 1,2-dichloroethane (3.6mL), and cool the mixture to 0°C, slowly drop A solution of chiral phosphoric acid (14.9 mg, 0.015 mmol) in 1,2-dichloroethane (0.4 mL) was added. After that, it was placed at 0°C and stirred for 48 hours.
[0056] The reaction solution was directly applied to silica gel column chromatography to obtain 72.1 mg of the target product Ib as a pale yellow foamy solid, with a calculated yield of 94%.
[0057] After the preparation of this step is completed, in order to further verify that the purified compound is indeed the target product to be prepared in this example, t...
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