Preparation method of alpha,beta-unsaturated carbonyl compound with high stereoselectivity and beta-sulfonylation
A carbonyl compound, stereoselective technology, applied in the field of drug synthesis, to achieve the effects of a wide range of substrates, simple operation and mild reaction conditions
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Embodiment 1
[0025] Synthesis of β-sulfonylated α,β-unsaturated carbonyl compounds EI of formula E:
[0026] First, 0.15 mmol of electron-deficient alkyne (1,3-Diphenyl-2-yn-1-one)(R 1 is phenyl, R 2 is phenyl), 0.3mmol of PhSO 2 Na(R 3 Phenyl) was added into 0.7mL of N,N dimethylformamide, continued to add 0.3mL of acetate buffer solution, stirred at room temperature, used UV and vanillin as color reagents, and monitored the reaction process with thin-layer chromatography until the end of the reaction. Then dilute with water, extract three times with 20mL ethyl acetate to obtain the organic phase, dry with anhydrous sodium sulfate and remove the solvent under reduced pressure to obtain the reaction crude product; finally use silica gel column chromatography to separate and purify the crude product, ethyl acetate:petroleum ether= 1:5 as the eluent to obtain the desired β-sulfonylated α,β-unsaturated carbonyl compound EI of the E formula, and the structural formula of EI is: Yield 9...
Embodiment 2
[0028] Synthesis of β-sulfonylated α,β-unsaturated carbonyl compounds EII of formula E:
[0029] Electron deficient alkyne (1-(3,4-dichlorophenyl)-3-phenyl-2-yn-1-one)(R 1 is 3,4-dichlorophenyl, R 2 is phenyl), 0.3mmol of PhSO 2 Na(R3 Phenyl) was added into 0.7mL of N,N dimethylformamide, continued to add 0.3mL of acetate buffer solution, stirred at room temperature, used UV and vanillin as color reagents, and monitored the reaction process with thin-layer chromatography until the end of the reaction. Then dilute with water, extract three times with 20mL ethyl acetate to obtain the organic phase, dry with anhydrous sodium sulfate and remove the solvent under reduced pressure to obtain the reaction crude product; finally use silica gel column chromatography to separate and purify the crude product, ethyl acetate:petroleum ether= 1:4 as the eluent to obtain the desired β-sulfonylated α,β-unsaturated carbonyl compound EII of the E formula, the structural formula of EII is ...
Embodiment 3
[0031] Synthesis of β-sulfonylated α,β-unsaturated carbonyl compound EⅢ of formula E:
[0032] First, 0.15 mmol of electron-deficient alkyne (1-naphthyl-3-phenyl-2-yn-1-one)(R 1 is naphthyl, R 2 is phenyl), 0.45mmol of PhSO 2 Na(R 3 phenyl) into 1.0mL N,N-dimethylformamide, continue to add 0.3mL acetate buffer solution and stir at room temperature, use UV and vanillin as color reagents, and monitor the reaction process with thin-layer chromatography until the end of the reaction. Then dilute with water, extract three times with 20mL ethyl acetate to obtain the organic phase, dry with anhydrous sodium sulfate and remove the solvent under reduced pressure to obtain the reaction crude product; finally use silica gel column chromatography to separate and purify the crude product, ethyl acetate:petroleum ether= 1:5 as the eluent to obtain the desired β-sulfonylated α,β-unsaturated carbonyl compound EⅢ, the structural formula of EⅢ is The yield is 91%, E / Z=99:1
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