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Asymmetric bismuth catalysis system, preparation method and application thereof

A catalytic system and asymmetric technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., can solve problems such as substrate limitations of asymmetric bismuth catalytic systems

Active Publication Date: 2019-04-09
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The invention provides an asymmetric bismuth catalytic system and its preparation method and application, which overcomes the limitations of the current asymmetric bismuth catalysis, can efficiently realize various types of asymmetric transformations, and solves the substrate limitation of the asymmetric bismuth catalytic system question

Method used

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  • Asymmetric bismuth catalysis system, preparation method and application thereof
  • Asymmetric bismuth catalysis system, preparation method and application thereof
  • Asymmetric bismuth catalysis system, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033]

[0034] With Bi(OAc) 3 / CPA catalytic system catalyzes the asymmetric allylation reaction of allylboronic acid pinacol ester (1.2equiv.) and isatin derivative ketimine (1.0equiv.) in ether solution at room temperature, the reaction The equation is as above. Bi(OAc) 3and chiral phosphoric acid (S)-A (the structure is shown in the dotted box on the right side) were added to the reaction tube, and then the substrate and the reaction solvent were added in sequence, stirred at room temperature, and the reaction was monitored by thin-layer chromatography. The consumption of catalyzer can be reduced to 1mol%, obtains 3-allyl-3-aminoindolinone with high yield and high enantioselectivity (99.5:0.5er (enantiomeric ratio, enantiomericratio)) up to 99% compound, and two drug molecules (+)-AG-041R and (-)-psychotriasine were obtained through a multi-step reaction.

Embodiment 2

[0036]

[0037] With Bi(OAc) 3 The / CPA catalytic system is a catalyst that catalyzes the asymmetric allylation reaction of cyclic N-sulfonyl ketimine (1.0 equiv.) and allyl boric acid pinacol ester (1.2 equiv.) as substrates at room temperature , the reaction equation is as above. Bi(OAc) 3 and chiral phosphoric acid (S)-A were added to the reaction tube, and then the substrate and the reaction solvent were added in turn, stirred at room temperature, and the reaction was monitored by thin-layer chromatography. The amount of catalyst can be reduced to 1 mol%, and the target product is obtained in 91% yield and 94:6 enantioselectivity.

Embodiment 3

[0039]

[0040] With Bi(OAc) 3 / CPA catalytic system catalyzes N-1-methylene naphthalene protected indole quinone (1.0 equiv.) and allylboronic acid pinacol ester (1.2 equiv.) as substrates in cyclohexane solution at room temperature The asymmetric reaction, the reaction equation is as above. Bi(OAc) 3 and chiral phosphoric acid (S)-B were added to the reaction tube, and then the substrate and the reaction solvent were added in turn, stirred at room temperature, and the reaction was monitored by thin-layer chromatography. A series of 3-allyl-3-oxindolinone compounds were obtained with a high yield of 99% and high enantioselectivity (98:2er).

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Abstract

The invention provides an asymmetric bismuth catalysis system, a preparation method and an application thereof, relates to the technical field of asymmetric catalysis and provides an asymmetric bismuth catalysis system. By adoption of the asymmetric bismuth catalysis system, the problem of high Substrate specificity of the bismuth catalysis system is solved. The asymmetric bismuth catalysis systemcomprises a metal activity center and a chiral ligand, wherein the metal activity center is selected from one or more of bismuth acetate, bismuth hydroxide, bismuth bromide or bismuth iodide; the chiral ligand is selected from chiral phosphoric acid. The asymmetric bismuth catalysis system is used for catalyzing multiple types of asymmetric transformations such as asymmetric allylation of ketoneand imine, asymmetric allylation of oxonium ions and asymmetric reaction of imine and phenolic substrates and the like.

Description

technical field [0001] The invention relates to the technical field of asymmetric catalysis, in particular to an asymmetric bismuth catalytic system and its preparation method and application. Background technique [0002] "Chirality" is a term used to express the asymmetry of compounds. It refers to the configuration of molecules or certain groups in molecules that can be arranged into two forms that are mirror images of each other but cannot overlap. [0003] In asymmetric synthesis, the most effective and most economical method is asymmetric catalytic reaction, which can obtain a large number of new optically active substances with only a small amount of chiral catalyst, so it has become a very useful method for synthesizing chiral compounds. An important research topic in the current asymmetric synthesis research field. With the research on asymmetric synthetic reactions getting more and more attention, chiral catalysts have become the hotspot and frontier of the whole ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07D275/06C07D487/04C07D209/38C07D209/40
CPCB01J31/1845B01J2531/0263B01J2531/54C07D209/38C07D209/40C07D275/06C07D487/04
Inventor 王杰李鑫
Owner NANKAI UNIV
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