Axial chirality bis-schiff base-containing ligand

A bi-Schiff base and axial chiral technology, which is applied in the field of compounds in the field of chemical technology, can solve the problems of large steric hindrance and limit the rotation angle of biphenyl, etc., and achieve the effect of high reactivity

Inactive Publication Date: 2009-03-25
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the ortho-position group of the biaryl axis of the axial chiral ligand containing bis-Schiff base proposed in this paper is a methyl group, which has a large steric hindrance, which limits the rotatable angle of the biphenyl, that is, limits the dihedral horn

Method used

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  • Axial chirality bis-schiff base-containing ligand
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  • Axial chirality bis-schiff base-containing ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (1) Preparation of compound II from compound IV (R 1 R 2 = Tert-butyl)

[0022] Compound IV (1.0 g, 4.1 mmol) and 3,5-di-tert-butyl salicylaldehyde (1.9 g, 8.2 mmol) were refluxed in ethanol for four hours. The solution produced a large amount of yellow solid. After the solvent was removed by filtration, the yellow solid was washed with cold ethanol and dried to obtain product II (2.38 g, 86%).

[0023] 1 H NMR(400MHz, CDCl 3 ) 13.07 (s, 2H, OH), 8.46 (s, 2H, CH=N), 7.39-7.08 (m, 10H, ArH), 3.81 (s, 6H, OCH 3 ), 1.37 (s, 18H), 1.21 (s, 18H).

Embodiment 2

[0025] (1) Preparation of compound III from compound V (R 1 R 2 = Tert-butyl)

[0026] Compound V (2.0 g, 8.2 mmol) and 3,5-di-tert-butyl salicylaldehyde (3.8 g, 16.4 mmol) were refluxed in ethanol for four hours. The solution produced a large amount of yellow solid. The solvent was removed by filtration, and the remaining yellow solid was washed with cold ethanol and dried to obtain product III (4.7 g, 85%).

[0027] 1 H NMR(400MHz, CDCl 3 ) 13.07 (s, 2H, OH), 8.46 (s, 2H, CH=N), 7.39-7.08 (m, 10H, ArH), 3.81 (s, 6H, OCH 3 ), 1.37 (s, 18H), 1.21 (s, 18H).

Embodiment 3

[0029] (1) Preparation of compound II from compound IV (R 1 R 2 =Chlorine)

[0030] Compound IV (1.0 g, 4.1 mmol) and 3,5-dichlorosalicylic aldehyde (1.6 g, 8.2 mmol) were refluxed in ethanol for six hours. After the reaction, the solvent was removed by filtration, and the remaining solid was washed with cold ethanol and dried to obtain product II (2.4 g, 85%).

[0031] 1 H NMR(400MHz, CDCl 3 ) 13.01 (s, 2H, OH), 8.46 (s, 2H, CH=N), 7.45-7.11 (m, 10H, ArH), 3.75 (s, 6H, OCH 3 ).

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Abstract

The invention relates to an axis chiral ligand containing bis-Schiff bases in the field of chemical technology, the structural formula thereof is as follows, in the formula, R1 equals to hydrogen, chlorine, methyl, ethyl, isopropyl, tertiary butyl or alkoxyl with1 to 3 carbons; R2 equals to hydrogen, chlorine, methyl, ethyl, isopropyl, tertiary butyl or alkoxyl with1 to 3 carbons. The invention has the axis chirality of biphenyl compounds, can be applied to asymmetric reactions catalyzed by metals, such as asymmetric cyclopropanation and the like, and has higher reactivity ( can achieve more than 90 percent ) and stereoselectivity ( can achieve more than 85 percent ).

Description

Technical field [0001] The invention relates to a compound in the technical field of chemical engineering, in particular to an axial chiral ligand containing a double Schiff base. Background technique [0002] Chiral ligands are the source of asymmetric induction and control of asymmetric catalysis. Excellent chiral ligands can not only effectively adjust the electronic properties of the active metal center, but also build a specific chiral microenvironment around the metal center. C 2 Axial chiral ligands are widely used in metal-catalyzed asymmetric reactions, such as asymmetric cyclopropanation reactions, due to their structural particularities. After 30 years of development, a large number of axial chiral ligands have emerged, such as BINAP is the most commonly used well-known ligand. Since the emergence of BINAP, scientists have devoted themselves to obtaining ligands that can not only possess good asymmetric reactivity and selectivity, but also can be synthesized by a simpl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/24C07C249/02C07B53/00
Inventor 王玲魏浩
Owner SHANGHAI JIAO TONG UNIV
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