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A kind of method of catalytic asymmetric oxidation thioether

A thioether oxidation, asymmetric technology, applied in the field of preparation of chiral sulfoxide, can solve the problems of restricting the industrial production of sulfide, and achieve the effect of fast reaction speed

Active Publication Date: 2019-02-19
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These problems have limited the industrial production of asymmetric oxidation of thioether

Method used

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  • A kind of method of catalytic asymmetric oxidation thioether
  • A kind of method of catalytic asymmetric oxidation thioether
  • A kind of method of catalytic asymmetric oxidation thioether

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Experimental program
Comparison scheme
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Embodiment 1

[0020] Investigation of reaction conditions

[0021]

[0022] At 25°C, Sc(OTf)3(1.0mg, 0.0021mmol) and L2(1.0mg, 0.0021mmol) were added to 1.0mL THF and stirred for 4h. The reaction mixture was cooled to 0°C, then added 0.42mmol thioether and 45% hydrogen peroxide (0.42mmol), and kept stirring at 0°C for 1h. Extracted with ethyl acetate, washed with 10% sodium thiosulfate solution, combined the organic phases, dried, analyzed by high performance liquid chromatography to obtain the ee value, obtained the product by column chromatography, and calculated the yield.

[0023] The reaction conditions were optimized using phenylmethyl sulfide as a model substrate. The results are shown in the table below.

[0024]

[0025] aIsolation yield. b Chiral HPLC detection.

[0026] It can be seen from the table that the solvent is tetrahydrofuran, the molar ratio of hydrogen peroxide to substrate thioether is 1.5:1, and the reaction temperature is -20°C, the result is the best. The...

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Abstract

The invention provides an asymmetric oxidation method of sulfide. Using a chiral complex formed by a tetradentate nitrogen organic ligand and a metal scandium compound as a catalyst, and using hydrogen peroxide as an oxidant, the asymmetric catalytic oxidation reaction of this type of sulfide is carried out to obtain the corresponding chiral sulfoxide compound. The enantioselectivities of the yields were all greater than 90%. The reaction is clean, with mild reaction conditions, high conversion and enantioselectivity. Has industrial prospects.

Description

technical field [0001] The invention relates to a method for preparing chiral sulfoxide by asymmetric oxidation of thioether. Background technique [0002] Chiral sulfoxide is an important intermediate in organic synthesis, which is widely used in the synthesis of fine chemicals such as drugs, spices, and food additives. Therefore, the preparation of chiral sulfoxide has important theoretical and practical significance. At present, the transition metal catalyzed asymmetric oxidation system of thioether reported in the literature mainly includes chiral diol (phenol)-titanium catalytic system, chiral triolamine-titanium, and chiral porphyrin metal complex catalytic system according to chiral ligands. , chiral Salen metal complex catalytic system and chiral Schiff alkali metal complex catalytic system (Arkivoc, 2011, (i), 1-110; Journal of Sulfur Chemistry, 2013, 34(3), 301-341). [0003] Although the above-mentioned systems can realize the asymmetric oxidation reaction of th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/02C07C317/14C07C317/22C07C317/18
CPCC07B2200/07C07C315/02C07C317/14C07C317/22C07C317/18
Inventor 高爽戴文李国松吕迎
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI