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Ionic compound containing chiral amine-thiourea (urea) and its preparation method and application

A technology of ionic compounds and chiral amines, applied in the directions of organic chemistry methods, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc. , The effect of wide application and low dosage

Active Publication Date: 2008-03-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Thiourea small-molecule catalysts have been widely used in asymmetric synthesis, while functionalized ionic compounds (such as chiral amine ionic compounds) have high catalytic activity, can be dissolved in green solvents (such as water, polyethylene glycol), and It can be reused many times, and it can also provide an ionic environment. Therefore, combining the advantages of the two, we designed and synthesized a series of ionic compounds containing chiral amine-thiourea (urea) structures, which have not been reported at home and abroad.

Method used

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  • Ionic compound containing chiral amine-thiourea (urea) and its preparation method and application
  • Ionic compound containing chiral amine-thiourea (urea) and its preparation method and application
  • Ionic compound containing chiral amine-thiourea (urea) and its preparation method and application

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Embodiment 1

[0034] Embodiment 1: Preparation of Chiral Ionic Compound 1

[0035] Add 3-methyl-2-((S)-pyrrolidinyl-2-methylthio)-3H-imidazolium bromide (1mmol), (3-phenyl-thioureido) sodium acetate into a 100mL Erlenmeyer flask (1mmol), THF (60mL) and water (30mL), stirred at room temperature for 24h, after the reaction was complete, desolvated under reduced pressure, then the solid was dissolved in 20mL of chloroform, filtered to remove inorganic salts, and the filtrate was distilled to remove the solvent to obtain The target compound (94% yield). Its specific rotation [α] D 20 =+45°.

Embodiment 2

[0036] Embodiment 2: Preparation of chiral ionic compound 2

[0037] Add 3-methyl-2-((S)-pyrrolidinyl-2-methylthio)-3H-imidazolium bromide (1mmol), (S)-3-phenyl-2- Sodium (3-phenyl-thioureido)propionate (1mmol), ethanol (10mL), stirred at room temperature for 24h, after the reaction was complete, the solid was dissolved in 20mL of chloroform, filtered to remove inorganic salts, and the filtrate was distilled off The target compound was obtained after solvent removal (yield 93%). Its specific rotation [α] D 20 =+28.4°.

Embodiment 3

[0038] Embodiment 3: Preparation of chiral ionic compound 3

[0039]Add 3-methyl-2-((S)-pyrrolidinyl-2-methylthio)-3H-imidazolium bromide (1mmol), (R)-3-phenyl-2-( 3-Phenyl-thioureido)sodium propionate (1mmol), methanol (60mL), stirred at room temperature for 24h, after the reaction was complete, desolvated under reduced pressure, then dissolved the solid in 20mL of chloroform, filtered to remove inorganic salts, and then The filtrate was distilled to remove the solvent to obtain the target compound (95%). Its specific rotation [α] D 20 =+28.4°.

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Abstract

The invention relates to an ion type compound containing a chiral amine-thiourea (urea) structure, the general formula is A plus B minus , wherein, the structure of A plus is shown as the formular (I), and the structure of B minus is shown as the formular (V). In a preparation method, the bromine salt of A plus and the sodium salt of B minus are resolved in organic solvent, under the room temperature, stiring continues untile the reaction is sufficient, and therefore the ion type compound containing a chiral amine-thiourea (urea) structure is produced. The substance of the invention can be used as not only a catalyst in an organic asymmetric reaction but also a chiral shift reagent in the chiral identification. The substance of the invention has a good chiral inducement property and can be used as a chiral reagent, a catalyst and a chiral material in the fields of organic synthesis, materials, etc.

Description

(1) Technical field [0001] The invention relates to a novel ionic compound containing a chiral amine-thiourea (urea) structure, and the invention also relates to a preparation method of the ionic compound containing a chiral amine-thiourea (urea) structure and its application in The application of symmetric catalytic synthesis, especially refers to the application of organic asymmetric reactions such as Michael reaction, Aldol reaction, Baylis-Hillman reaction or Michael-Aldol tandem reaction. In addition, it also relates to the application of ionic compounds with chiral amine-thiourea (urea) structure as chiral displacement reagents in chiral recognition. (2) Background technology [0002] Chirality is one of the essential properties of nature and the basis of all life. The chiral synthesis (asymmetric synthesis) reaction is an indispensable method and means for the synthesis of chiral substances. Catalytic asymmetric synthesis is the most ideal asymmetric synthesis metho...

Claims

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Application Information

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IPC IPC(8): C07D403/12C07D403/06C07D401/06C07D207/09B01J31/02B01J31/04C07B53/00
Inventor 许丹倩岳华栋罗书平王益锋徐振元
Owner ZHEJIANG UNIV OF TECH
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