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5,5' bit connected 1,1'-diphenyl kind axle chirality ligand

An axial chirality and ligand technology, applied in the field of 1, compounds, can solve problems such as limiting the rotation angle of biphenyl, and achieve the effect of good application prospect, high reactivity and stereoselectivity

Inactive Publication Date: 2006-06-28
SHANGHAI JIAO TONG UNIV
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Problems solved by technology

[0003] Through literature retrieval to prior art, E.J.Corey et al published "The First Enantioselective Synthesis of the Chemotactic Factor Sirenin by an Intramolecular [2+1]Cyclization Using a New Chiral Catalyst" (a new type of chiral catalyst realized the enantioselective synthesis of Sirenin for the first time through the intramolecular [2+1] cyclization reaction), the chiral catalyst proposed in this paper The design concept of sexual ligands is to add two larger groups to the ortho-position of the biaryl axis to obtain stable axial chirality through their steric hindrance, but also limit the angle at which the biphenyl can rotate, that is limited dihedral angle

Method used

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  • 5,5' bit connected 1,1'-diphenyl kind axle chirality ligand
  • 5,5' bit connected 1,1'-diphenyl kind axle chirality ligand
  • 5,5' bit connected 1,1'-diphenyl kind axle chirality ligand

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Embodiment Construction

[0024] The following examples will help to further understand the present invention, but do not limit the content of the present invention.

[0025] (1) Preparation of compound IV from 2-bromo-4-methoxybenzophenone

[0026] Under ice bath, slowly drop bromine (2.8mL, 35.1mmol) into NaOH (4.5g, 111.4mmol) aqueous solution (10mL), stir for 10min, then add 2-bromo-4-methoxybenzophenone (2.1 g, 9.2mmol) was dropped into the above reaction solution and stirred at room temperature for 15h. After the reaction finishes, add aqueous sodium sulfite to eliminate unreacted sodium hypobromite. The neutral compound was separated by extraction with ethyl acetate, and the aqueous phase was acidified with 6N hydrochloric acid in an ice bath, and a large amount of white solid appeared. Filtration afforded IV as a white solid (2.0 g, 95%).

[0027] 1 H NMR (CDCl 3 , 300MHz) 8.05 (d, J = 8.7Hz, 1H, Ar-H), 7.23 (d, J = 2.7Hz, 1H, Ar-H), 6.91 (dd, J = 8.7, 2.7Hz, 1H, Ar- H), 3.87(s, 3H, OCH ...

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Abstract

The invention relates to 5, 5í» connecting 1, 1í»-biphenyl class axis chirality ligand that belongs to chemical field. It contains center chirality in oxazolines and axis chirality of biphenyl class. It has high activity and solid selection in asymmetry reaction and has bright application prospect.

Description

technical field [0001] The invention relates to a compound in the technical field of chemical industry, in particular to a 1,1'-biphenyl-type axial chiral ligand connected at the 5,5' position. Background technique [0002] The key to asymmetric catalytic synthesis is how to design and synthesize chiral catalysts with high selectivity and catalytic activity, in which chiral ligands are the source of asymmetric induction and control of catalysts. C 2 Chiral bisoxazoline ligands, due to their special structure, are widely used in metal-catalyzed asymmetric reactions, such as asymmetric cyclopropanation, intramolecular Wacker-Type cyclization, asymmetric alkene Oxidation reactions and intramolecular [2+1] cycloaddition reactions, etc. After 30 years of development, a large number of chiral oxazoline ligands have emerged, especially chiral oxazoline ligands with various chiral side chains have been developed. Among them, the axial chiral side chain has been widely used in lig...

Claims

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Application Information

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IPC IPC(8): C07D413/14
Inventor 张万斌张勇健王飞军
Owner SHANGHAI JIAO TONG UNIV
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