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Method for synthesizing chiral boron compound containing trifluoromethyl and compound

A technology of trifluoromethyl group and synthesis method is applied in the field of synthesis of trifluoromethyl group-containing chiral boron compounds, and achieves the effects of easy preparation, easy availability of raw materials and simple operation.

Inactive Publication Date: 2017-01-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, β-trifluoromethyl-α,β-unsaturated ketones have not been applied to asymmetric borylation reactions, and their products contain carbon chiral centers linked to trifluoromethyl groups, which have potential biological activity.

Method used

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  • Method for synthesizing chiral boron compound containing trifluoromethyl and compound
  • Method for synthesizing chiral boron compound containing trifluoromethyl and compound
  • Method for synthesizing chiral boron compound containing trifluoromethyl and compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] Under nitrogen protection, copper iodide CuI (1.9mg, 0.01mmol), (R,S)-Josiphos (9.6mg, 0.015mmol), potassium phosphate K 3 PO 4 (4.2mg, 0.02mmol), pivalyl alcohol t-AmOH (1.0mL), after stirring at room temperature for 30 minutes, add bis-pinacolyl diborane 3 (55.9mg, 0.22mmol) and pivalyl alcohol t-AmOH (0.5 mL), stirred at room temperature for 10 minutes. Then (E)-4,4,4-trifluoro-1-p-tolyl-2-en-1-one 2a and pivalyl alcohol t-AmOH (0.5 mL) were added, and stirred at 60° C. for 20 hours. After cooling to room temperature, filter through diatomaceous earth, wash the filter cake with ethyl acetate (20 mL), and concentrate the filtrate under reduced pressure. After separation by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=60:1), the white solid product 1a (43mg, yield 63%, ee value 93% ). The target product was confirmed by NMR and high-resolution mass spectrometry, and the ee value was determined by chiral high-per...

Embodiment 2

[0037] The reaction steps and operation are the same as in Example 1, except that the copper salt is cuprous bromide. The reaction was stopped, and the target product 1a (39 mg, yield 58%, ee value 93%) was obtained after post-processing. It shows that cuprous bromide can also be used as a catalyst for the reaction, but it is not the best catalyst.

Embodiment 3

[0039] The reaction steps and operation are the same as in Example 1, and the difference from Example 1 is that the copper salt is cuprous chloride. The reaction was stopped, and the target product 1a (6 mg, yield 9%) was obtained after post-processing. It shows that cuprous chloride can also be used as a catalyst for the reaction, but it is not the best catalyst.

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Abstract

The invention discloses a method for synthesizing a chiral boron compound containing trifluoromethyl and having a potential biological activity. With beta-trifluoromethyl-alpha,beta-unsaturated ketone and bis(pinacolato)diborane as raw materials, and a chiral ligand copper salt as a catalyst, an asymmetric boronizing reaction is carried out for synthesis of the chiral boron compound. Compared with a reported method for synthesizing the chiral boron compound, the method has the advantages of easily obtained raw materials, simple operation, wide application range and mild reaction conditions, the product contains a carbon chiral center connected with trifluoromethyl, and the product has the potential biological activity.

Description

technical field [0001] The invention discloses a synthesis method of a chiral boron compound containing trifluoromethyl with potential biological activity. Using β-trifluoromethyl-α,β-unsaturated ketone and bis-pinacolyl diborane as raw materials and chiral ligand copper salt as catalyst, chiral boron compounds were synthesized by asymmetric boronation. Compared with the reported methods for synthesizing chiral boron compounds, the present invention has easy-to-obtain raw materials, simple operation, wide application range and mild reaction conditions, and the product contains a carbon chiral center linked to a trifluoromethyl group and has potential biological activity. Background technique [0002] Chiral boron compounds are important organic reagents and have a wide range of applications in the fields of industry, agriculture, and medicine. The trifluoromethyl group is an extremely important functional group, which can greatly change the biological activity and physical ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04C07B53/00
Inventor 余正坤姜权彬
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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