Beta-chiral carbonyl compound as well as preparation method and application thereof
A carbonyl compound and chiral technology, which is applied in the field of β-chiral carbonyl compounds and their preparation, can solve the problems of limited application range, harsh preparation conditions and complicated process of β-chiral carbonyl compounds, and achieve the expansion of designability and application prospects, high forward reaction rate, and simplified operation steps
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[0073] On the other hand, on the basis of the above-mentioned β-chiral carbonyl compound of the present invention, the embodiment of the present invention also provides a preparation method of the above-mentioned β-chiral carbonyl compound of the general formula I. Including the following steps:
[0074] S01 : respectively provide nucleophilic reagent compound A, conjugated alkenal compound B and functional group reagent C represented by the following structural formula:
[0075] A: B: C:
[0076] S02 : The nucleophile compound A, the conjugated enaldehyde compound B, and the functional grouping agent C are added to a reaction system containing an azacarbene catalyst and an alkali reagent, and the β-asymmetric functionalization reaction is carried out to obtain the following structural formula: The β-chiral carbonyl compound shown in the following formula I:
[0077]
[0078] In the above step S01, R in the molecular structural formula of the nucleophile compound ...
Embodiment 1
[0099] This example provides a chiral S-phenethyl-4,4,4-trifluoro-3-(2-thienyl)thiobutyrate and a preparation method thereof. The structural formula of the S-phenethyl-4,4,4-trifluoro-3-(2-thienyl)thiobutyrate is shown in the following molecular structural formula I1:
[0100]
[0101] Its preparation steps are as follows:
[0102] Add mesitylene-substituted indenol-derived triazolecarbene catalyst (0.01mmol, 0.1eq), quinuclidine (0.12mmol, 1.2eq), biphenol phosphate (0.02mmol, 0.2eq) into a dry 10mL test tube, 100 mg of preactivated powdered molecular sieves and 1.0 mL of anhydrous toluene were replaced with argon three times, and the reaction tube was sealed and stirred at room temperature for 10 min. Phenylthiol (0.125mmol, 1.25eq) was slowly added to the reaction system and stirred at room temperature for 0.5 hours. The corresponding β-trifluoromethyl-substituted alkenal substrate (0.1 mmol, 1.0 eq) was slowly added to the reaction system, and the resulting mixture wa...
Embodiment 2
[0104] This example provides a chiral S-phenethyl-3-(5-benzo[1,3]dioxolyl)thiobutyrate and a preparation method thereof. The structural formula of the S-phenethyl-3-(5-benzo[1,3]dioxolyl)thiobutyrate is shown in molecular structural formula I2 below:
[0105]
[0106] Its preparation steps are as follows:
[0107] Add mesitylene-substituted indenol-derived triazolecarbene catalyst (0.01mmol, 0.1eq), quinuclidine (0.12mmol, 1.2eq), biphenol phosphate (0.02mmol, 0.2eq) into a dry 10mL test tube, 100 mg of preactivated powdered molecular sieves and 1.0 mL of anhydrous toluene were replaced with argon three times, and the reaction tube was sealed and stirred at room temperature for 10 min. Phenylthiol (0.125mmol, 1.25eq) was slowly added to the reaction system and stirred at room temperature for 0.5 hours. The corresponding β-methyl-substituted alkenal substrate (0.1 mmol, 1.0 eq) was slowly added to the reaction system, and the resulting mixture was stirred at room temperatu...
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