Soluble chiral diamino derivative, its production and use

A chiral diamine and water-soluble technology, which is applied in the field of chiral diamine and its derivatives, can solve the problems of inability to form micelles or capsules, unfavorable special microreaction environment and stable holes, etc.

Inactive Publication Date: 2007-11-21
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Amphiphilic compounds are usually dispersed in organic solvents and cannot form micelles or capsules, which is not conducive to the formation of special microreaction environments or stable holes

Method used

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  • Soluble chiral diamino derivative, its production and use
  • Soluble chiral diamino derivative, its production and use
  • Soluble chiral diamino derivative, its production and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Example 1 Asymmetric transfer hydrogenation of acetophenone in aqueous phase catalyzed by complexes of ruthenium and I

[0074] 1.2mg (0.002mmol) of [RuCl 2 (p-cymene)] 2 and 1.7mg (0.0044mmol) of water-soluble ligand N-tosylated-1,2-bis-(2'-aminophenyl)-1,2-ethylenediamine were added to 1mL of water and activated at 40°C 1 hour. At room temperature, 208mg (2.0mmol) HCOONa·2H 2 O and 48 μL (0.4 mmol) of acetophenone were added to the system and reacted for 0.5 hours. Then use CH 2 Cl 2 After extraction several times, the extract was dried with anhydrous sodium sulfate, filtered and concentrated, and the conv. and ee values ​​were determined by GC (33% conv., 95% ee).

Embodiment 2

[0075] The asymmetric transfer hydrogenation reaction of acetophenone in the water phase that the complex of iridium and I catalyzes the embodiment two

[0076] 1.6mg (0.002mmol) of [IrCl 2 (cp * )] 2 and 1.7mg (0.0044mmol) of water-soluble ligand N-tosylated-1,2-bis-(2'-aminophenyl)-1,2-ethylenediamine were added to 1mL of water and activated at 40°C 1 hour. At room temperature, 208mg (2.0mmol) HCOONa·2H 2 O and 48 μL (0.4 mmol) of acetophenone were added to the system and reacted for 0.5 hours. Then use CH 2 Cl 2 After extraction several times, the extract was dried with anhydrous sodium sulfate, filtered and concentrated, and the conv. and ee values ​​were determined by GC (29% conv., 95% ee).

[0077] Asymmetric transfer hydrogenation of acetophenone in aqueous phase catalyzed by complexes of rhodium and I

Embodiment 3

[0079] 1.3mg (0.002mmol) of [RhCl 2 (cp * )] 2 and 1.7mg (0.0044mmol) of water-soluble ligand N-tosylated-1,2-bis-(2'-aminophenyl)-1,2-ethylenediamine were added to 1mL of water and activated at 40°C 1 hour. At room temperature, 41.6mg (0.4mmol) HCOONa·2H 2 O and 48 μL (0.4 mmol) of acetophenone were added to the system and reacted for 0.5 hours. Then use CH 2 Cl 2 After extraction several times, the extract was dried with anhydrous sodium sulfate, filtered and concentrated, and the conv. and ee values ​​were determined by GC (86% conv., 97% ee).

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Abstract

The invention relates to a soluble chiral diamino derivative, use and a preparation thereof, belongs to the organic chemistry field. A water-soluble chiral diamine-pure optical N-monosulfonated acylation-1,2-2-(2'-amino-phenyl)-1,2-ethylenediamine and its derivative or its salt, their uses and productions are disclosed. It's fast, simple, no need for other organic solvents or additives and has better effect than organic phase. Complex formed of the soluble chiral diamine and metal can be used for ketone and imine asymmetric catalytic hydrogenating reduction in aqueous phase.

Description

technical field [0001] The invention relates to a class of novel water-soluble chiral diamine and its derivatives, as well as the application and preparation method in asymmetric catalysis, belonging to the field of organic chemistry. Background technique [0002] Green chemistry research is directly related to the sustainable development of human society, and the catalytic reaction in aqueous solution has always been the focus and hotspot of green chemistry research. Water has many advantages as a solvent: First, it is cheap and easy to obtain, safe and reliable, non-toxic and pollution-free. Second, the product can be isolated by simple phase separation. However, in the reaction with organic solvent as the medium, the separation of products often consumes a lot of energy, and a large amount of organic solvent is discharged during the production process, which causes serious pollution to the environment. Third, water-phase catalyzed reactions often have some special react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/18C07C303/36B01J31/22B01J31/28C07B53/00
CPCY02P20/55
Inventor 邓金根李利朱槿薛东廖建
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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