Amino group-containing chiral ionic liquid and its prepn process and application

A chiral ionic liquid and amino group-containing technology, applied in the field of chiral ionic liquids, can solve the problems of difficult recovery of catalyst, decrease in yield and ee value, etc., and achieve excellent chiral catalytic performance, good steric hindrance, and convenience. Repeated effects

Inactive Publication Date: 2006-10-18
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In 2000, Hanessian et al. discovered that L-proline can chirally catalyze the asymmetric Michael reaction between nitroalkyl and enone (Organic Lett., 2000, 2, 2975). Soon after, Barbas et al. used (5) in the asymmetric The Michael addition reaction has a good catalytic effect, and the ee value of the product can reach 91% (Tetrahedron Lett., 2001, 42, 4441). At the same time, (6) asymmetric Michael reaction of aldehydes and nitroviny...

Method used

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  • Amino group-containing chiral ionic liquid and its prepn process and application
  • Amino group-containing chiral ionic liquid and its prepn process and application
  • Amino group-containing chiral ionic liquid and its prepn process and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Example 1 Preparation of 1-[(2S)-2-aminopropyl]-3-hexylimidazolium bromide

[0053] Add (S)-1-(bromomethyl)ethylamine hydrobromide (22.12g, 0.1mol), N-hexylimidazole (15.51g, 98%, 0.1mol) and ethanol (60mL) into a 100mL three-necked flask, Reflux reaction for 20 h, neutralize and precipitate under reduced pressure, wash with ethyl acetate (2×20 mL), and distill off the solvent to obtain the target ammonium halide salt (27.55 g, yield 95%).

Embodiment 2

[0054] Example 2 Preparation of 1-[(2S)-2-amino-3-methylpentyl]-2-methyl-3-methylimidazolium chloride salt

[0055] Add (S)-1-(chloromethyl)-2-methylbutylamine hydrochloride (17.37g, o.1mol), 1,2-dimethylimidazole (7.84g, 98%, 0.08mol) and acetonitrile (60mL), reflux reaction 40h, decompression precipitation after neutralization, wash (2 * 20mL) with ethyl acetate, obtain target ammonium halide salt (16.67g, yield 90 %).

Embodiment 3

[0056] Example 3 Preparation of 1-[(2S)-2-amino-4-methylhexyl]-3-ethylimidazolium bromide

[0057] Add (S)-1-(bromomethyl)-3-methylpentylamine hydrobromide (26.36g, 0.1mol) and N-ethylimidazole (10.78g, 98%, 0.11mol) into a 100mL three-necked flask and ethanol (60mL), reflux reaction for 24h, neutralization, precipitation under reduced pressure, washing with ethyl acetate (2×20mL), and distillation to remove the solvent to obtain the target ammonium halide salt (26.50g, yield 96%).

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Abstract

The present invention relates to amino group-containing chiral ionic liquid and its preparation process and application in organic asymmetrical catalytic Michael reaction. The chiral ionic liquid has the general expression of A+B-, A+ is shown, and B- is halogen ion or other negative ions as shown. The preparation process includes the following steps: the reflux reaction between amino acid derived halogenated fatty amine haloid and substituting imidazole in organic solvent, and the neutralization of the reacted liquid to obtain the product. The chiral ionic liquid with connected imidazole cycle possessing excellent stereo steric hindrance effect has excellent chiral catalytic performance on Michael reaction except its application as common ionic liquid.

Description

(1) Technical field [0001] The invention relates to an amino group-containing chiral ionic liquid, a preparation method and an application thereof. (2) Background technology [0002] Asymmetric synthesis has become an important research direction of chemistry in the 21st century and an indispensable part of the fields of organic synthetic chemistry, biochemistry, medicinal chemistry and pesticide chemistry. Usually, asymmetric synthesis reactions are realized by using chiral auxiliary agents, chiral reagents and chiral catalysts. Catalytic asymmetric synthesis is the most ideal asymmetric synthesis method, it only uses a small amount of chiral catalyst to obtain a large number of chiral products. Chiral catalysts can be divided into chiral organic complex metal catalysts, enzymes and chiral organic molecular catalysts. Chiral organic molecular catalysts are increasingly valued because they are environmentally friendly and do not use expensive transition metals and chiral li...

Claims

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Application Information

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IPC IPC(8): C07B53/00C07D233/64C07D403/06C07F5/02C07F9/6506
Inventor 许丹倩罗书平徐振元沈寅初
Owner ZHEJIANG UNIV OF TECH
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