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Axial chirality diphosphine ligand containing bis-schiff base

A technology of bis-Schiff base and bis-phosphine ligand, which is applied in the chemical field of chemical technology, can solve the problems of large steric hindrance, 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

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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 diphosphine ligand containing bis-schiff base

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Effect test

Embodiment 1

[0017] (1) Preparation of Compound II from Compound IV

[0018] Compound IV (1.0g, 4.1mmol) and 2-diphenylphosphinebenzaldehyde (2.38g, 8.2mmol) were refluxed in toluene for fourteen hours, and purified by column chromatography to obtain the product II ( 2.9 g, 89%).

[0019]

[0020] 1 H NMR (CDCl 3 400, MHz) δ 8.93(d, 2H, N=CH, J=5.6Hz), 7.78-6.69(m, 32H, ArH), 6.35(d, 2H, ArH), 3.82(s, 6H, OCH 3 ) 31 P NMR (CDCl 3 , 161MHz) δ-14.17

Embodiment 2

[0022] (1) Preparation of Compound III from Compound V

[0023] Compound V (2.0g, 8.2mmol) and 2-diphenylphosphinebenzaldehyde (4.76g, 16.4mmol) were refluxed in toluene for fourteen hours, and purified by column chromatography to obtain product III ( 5.7 g, 87%).

[0024]

[0025] 1 H NMR (CDCl 3 400, MHz) δ 8.93(d, 2H, N=CH, J=5.6Hz), 7.78-6.69(m, 32H, ArH), 6.35(d, 2H, ArH), 3.82(s, 6H, OCH 3 ) 31 P NMR (CDCl 3 , 161MHz) δ-14.18

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Abstract

The invention relates to an axis-chiral double phosphine ligand containing double schiff bases in the chemical technical field; the structural formula is shown as follows. The axis-chiral double phosphine ligand comprises the axis-chiral of biphenyl, can be used in all metal accelerating asymmetric reactions such as asymmetric epoxidation reaction of olefin, asymmetric cyclopropanation and the like, and has higher reactivity (can reach over 70 percent ) and stereoselectivity (can reach over 80 percent).

Description

technical field [0001] The invention relates to a compound in the technical field of chemical engineering, in particular to an axial chiral bis-Schiff base-containing bisphosphine ligand. Background technique [0002] Chiral ligands are the source of asymmetric induction and control in asymmetric catalysis. Excellent chiral ligands can not only effectively regulate the electronic properties of active metal centers, but also construct specific chiral microenvironments around metal centers. C 2 Axonal chiral bisphosphine ligands are widely used in various asymmetric reactions catalyzed by metals due to their special structure. After 30 years of development, a large number of bisphosphine ligands have emerged. After years of research, the axial chiral bisphosphine ligand BINAP containing the binaphthyl structure has been successfully applied to the industrial production of optically active compounds. Since the emergence of BINAP, scientists have been committed to obtaining l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/50B01J31/24C07B53/00
Inventor 王玲魏浩
Owner SHANGHAI JIAO TONG UNIV
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