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Preparation method of bidentate oxazoline chiral ligands

A technology of bidentate oxazolines and chiral ligands, which is applied in the field of preparation of bidentate oxazoline chiral ligands, and can solve the problem of not mentioning the preparation method of bidentate oxazoline chiral ligands, which is difficult to find Synthetic strategies and other issues to achieve high yield, rational design, and optimized reaction conditions

Active Publication Date: 2020-09-01
INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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Problems solved by technology

[0006] Yet, do not mention the preparation method of this novel and efficient bidentate oxazoline class chiral ligand (formula IA) in this document
Although some typical organic synthesis methods, such as the classic name reaction, have been widely used to prepare the desired target compounds, based on the feedback received so far, researchers in the field of organic synthesis seem to be preparing this In the process of ligand-like, it is still difficult to find an effective synthetic strategy to ensure the chiral configuration of the ligand and obtain the aforementioned ligand in the required amount

Method used

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  • Preparation method of bidentate oxazoline chiral ligands
  • Preparation method of bidentate oxazoline chiral ligands
  • Preparation method of bidentate oxazoline chiral ligands

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Embodiment Construction

[0047] Below in conjunction with specific embodiment, the present invention is described in further detail. In the specific examples below, unless otherwise specified, the reagents used can be purchased by those skilled in the art through conventional commercial channels.

[0048] The synthesis of the bidentate oxazoline chiral ligand shown in embodiment 1 formula I-1 (synthetic route one)

[0049] Synthesis of step 1 formula B compound (Ar=Ph)

[0050] at room temperature and N 2 Under protection, 3,5-dibromobenzaldehyde 29 (5.28g, 20mmol), phenylboronic acid (6.10g, 50mmol), sodium carbonate (10.60g, 100mmol) in H 2 To a solution in O / PhMe (50ml / 50ml) was added tetrakis(triphenylphosphine)palladium (0.23g, 0.2mmol). The reaction mixture was then stirred at 120 °C and the progress of the reaction was checked by TLC. Upon completion, the mixture was extracted with EtOAc, then the organic layer was separated, dried over magnesium sulfate and concentrated. Finally, the mixt...

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Abstract

The invention discloses a preparation method of bidentate oxazoline chiral ligands, which uses simple, economical and cheap initial raw materials and organic synthesis reagents, reasonably designs thesynthesis route and optimizes the reaction conditions to conveniently prepare the bidentate oxazoline chiral ligands as shown in formulas I-1 and I-2 at high yield.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, and in particular relates to a preparation method of a bidentate oxazoline chiral ligand. Background technique [0002] Chirality is one of the most important properties of nature. Nucleotides, amino acids, and monosaccharides, the basic substances of life in nature, and the biological macromolecules nucleic acids, proteins, and sugars composed of them all have unique chiral characteristics. Many physical, chemical, and biological functions originate from the precise identification and strict matching of molecular chirality, such as the relationship between the chirality of chiral drugs and their biological responses. In the field of chemical pharmacy, the chirality of drug compounds is directly related to the pharmacological action, clinical effect, toxic and side effects, drug effect and drug effect time of the drug. For example, different enantiomers show different activities (suc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/12
CPCC07D263/12C07B2200/07Y02P20/55
Inventor 钱鹏程范茂盛叶龙武张景峰陈帆
Owner INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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