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Chiral tridentate imine P, N, N-ligand, preparation method and application of chiral tridentate imine P, N, N-ligand in Cu-catalyzed asymmetric propargyl conversion

A technology of tridentate imine and chirality, which is applied in the field of novel chiral tridentate imine P,N,N-ligands and its preparation, can solve the problems of limited chiral ligands, and achieve easy modification of structure and properties The effect of stability and simple preparation method

Active Publication Date: 2022-05-27
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the chiral ligands suitable for Cu-catalyzed asymmetric propargyl conversion reactions are still very limited, and many Cu-catalyzed asymmetric propargyl conversion reactions have not yet achieved satisfactory research results. The development of new and efficient chiral ligands Sexual ligands remain at the heart of Cu-catalyzed asymmetric propargyl conversion reactions

Method used

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  • Chiral tridentate imine P, N, N-ligand, preparation method and application of chiral tridentate imine P, N, N-ligand in Cu-catalyzed asymmetric propargyl conversion
  • Chiral tridentate imine P, N, N-ligand, preparation method and application of chiral tridentate imine P, N, N-ligand in Cu-catalyzed asymmetric propargyl conversion
  • Chiral tridentate imine P, N, N-ligand, preparation method and application of chiral tridentate imine P, N, N-ligand in Cu-catalyzed asymmetric propargyl conversion

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 Consisting of chiral ferrocene-1,2-diphenylethylenediamine compound (R c ,S p ,S c ,S c-II-1 and 2-pyridinecarboxaldehyde III-1 are raw materials for the preparation of chiral tridential P, N, N-imine ligands (R c ,S p ,S c ,S c )-I-1。

[0031]

[0032] Under nitrogen protection, chiral ferrocene-1,2-diphenylethylenediamine compound (R. 2-diphenylethylenediamine compound) was added to the reaction bottle c ,S p ,S c ,S c -II-1 (1.0mmol, 1.0equiv), 2-pyridinecarboxaldehyde III-1 (1.0mmol, 1.0equiv) and Anhydrous Na 2 SO 4 (2.0mmol, 2.0equiv), add 5.0mL of anhydrous toluene, reflux stirring reaction for 24h. After the reaction, the silica gel column is separated by chromatography, the vacuum is dried to obtain a yellow solid, and the yield is 81%.

[0033] Chiral tridenta P, N, N-imine ligand (R c ,S p ,S c ,S c Nuclear magnetic resonance hydrogen spectroscopy and phosphorus spectroscopy of I-1 such as Figure 1 、 Figure 2 As shown: 1 H NMR(400MHz,CDCl 3 )δ8.54–6....

Embodiment 2

[0034] Example 2 Ethanol prepared as a reaction solvent (R c,S p ,S c ,S c )-I-1

[0035] The solvent toluene in Example 1 is replaced with ethanol, the rest is the same as Example 1. The reaction yields (R c ,S p ,S c ,S c -I-1,74% yield.

Embodiment 3

[0036] Example 3 Methanol prepared as a reaction solvent (R c ,S p ,S c ,S c )-I-1

[0037] The solvent toluene in Example 1 is replaced with methanol, the rest is the same as Example 1. The reaction yields (R c ,S p ,S c ,S c -I-1, 42% yield.

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Abstract

The invention provides a chiral tridentate imine P, N, N-ligand, a preparation method and an application of the chiral tridentate imine P, N, N-ligand in Cu-catalyzed asymmetric propargyl conversion, the chiral tridentate imine P, N, N-ligand has stable properties, has good tolerance to air and humidity and contains N-H functional groups, and the chiral tridentate imine P, N, N-ligand is prepared from chiral ferrocenephosphine-1, 2, 3, 4-tetramethyl-1, 3, 4-tetramethyl-1, 3, 4-tetramethyl-1, 3, 4-tetramethyl-1, 3, 4-tetramethyl-1, 3, 4-tetramethyl-1, 3, 4 A 1, 2-diphenylethylenediamine compound and a 2-acyl pyridine compound are used as raw materials, and one-step reaction is performed under mild conditions under the action of a dehydrating agent. The catalyst composed of the novel chiral tridentate imine P, N, N-ligand and a Cu metal precursor has excellent catalytic activity and stereoselectivity in an asymmetric propargyl conversion reaction.

Description

Technical field [0001] The present invention relates to the field of organic synthesis, specifically to a new chiral tridentimide P, N, N- ligand and preparation method and application thereof applied to cu- catalytic asymmetric propylene conversion reaction containing N-H functional groups. Background [0002]Cu-catalyzed asymmetric propyl conversion reaction has flourished over the past decade or so as one of the important and efficient methods for constructing alkynyl-containing chiral compounds and chiral ring-like skeletons [(a)Ljungdahl, N.; Kann, N.Transition-Metal-Catalyzed Propargylic Substitution.Angew.Chem., Int.Ed.2009, 48,642-644.(b)Miyake,Y.；Uemura,S.；Nishibayashi,Y.CatalyticPropargylic Substitution Reactions.ChemCatChem 2009,1,342-356. (c) Ding,C.-H.；Hou,X.-L.Catalytic Asymmetric Propargylation.Chem.Rev.2011,111,1914-1937. (d) Hu,X.-H.；Liu,Z.-T.；Shao,L.；Hu,X.-P.Recent Advances in CatalyticStereocontrolled Cycloaddition with Terminal Propargylic Compounds.Synthesis2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02B01J31/24B01J31/22B01J31/18C07C67/343C07C69/94
CPCC07F17/02B01J31/2404B01J31/2295B01J31/189C07C67/343C07B2200/07B01J2531/16B01J2531/842B01J2531/0225B01J2531/0238B01J2531/0261B01J2231/4205C07C69/94Y02P20/55
Inventor 胡向平万银波
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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