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Preparation method and application of chiral tertiary alcohol or tertiary ether compound

A technology for ketone compounds and compounds is applied in the field of preparation of chiral tertiary alcohols or tertiary ether compounds, which can solve the problems of unfavorable industrial application, unstable compounds, etc., and achieves high regioselectivity and stereoselectivity, good catalysis Active, mild effect of reaction conditions

Active Publication Date: 2017-11-24
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the raw material that this method uses, vinyl oxirane compound is unstable, is unfavorable for the industrialized application of reaction

Method used

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  • Preparation method and application of chiral tertiary alcohol or tertiary ether compound
  • Preparation method and application of chiral tertiary alcohol or tertiary ether compound
  • Preparation method and application of chiral tertiary alcohol or tertiary ether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] This example provides the preparation of chiral tertiary alcohol Ic, in which the preparation results using different boron compounds are given.

[0040] Add Pd to the reaction tube sequentially 2 (dba) 3 CHCl 3 (0.025mmol), chiral ligand 2a[X=N(iPr)] (0.1mmol), boron compound (0.2mmol), compound IIIc (1.0mmol), water (10mmol) and tetrahydrofuran (5.0mL), 40°C The reaction was carried out for 16 hours. After the solvent was evaporated under reduced pressure, the residue was subjected to column chromatography to obtain the corresponding chiral tertiary alcohol Ic.

[0041] The reaction formula of this embodiment and the results of preparing chiral tertiary alcohol compound Ic using different boron compounds are as follows:

[0042]

Embodiment 2

[0044] This example provides the preparation of chiral tertiary alcohol compound Ic or IIc, in which the preparation results using different ligands are given.

[0045] Add Pd to the reaction tube sequentially 2 (dba) 3 CHCl 3 (0.025mmol), chiral ligand (0.1mmol), phenylboronic acid (0.2mmol), compound IIIa (1.0mmol), water (10mmol) and tetrahydrofuran (5.0mL), react at 40°C for 16 hours. After the solvent was evaporated under reduced pressure, the residue was subjected to column chromatography to obtain the corresponding chiral tertiary alcohol compound Ic or IIc.

[0046] The reaction formula of this example and the results of preparing chiral tertiary alcohol compounds Ic or IIc using different ligands are as follows:

[0047]

[0048] serial number

Embodiment 3

[0050] This example provides the preparation of chiral tertiary alcohol compound Ic or IIc, in which the preparation results using different solvents are given.

[0051] Add Pd to the reaction tube sequentially 2 (dba) 3 CHCl 3 (0.025mmol), chiral ligand 3a (0.1mmol), phenylboronic acid (0.2mmol), compound IIIc (1.0mmol), water (10mmol) and solvent (5.0mL), react at 40°C for 16 hours. After the solvent was evaporated under reduced pressure, the residue was subjected to column chromatography to obtain the corresponding chiral tertiary alcohol compound Ic or IIc.

[0052] The reaction formula of this embodiment and the results of preparing chiral tertiary alcohol compound Ic using different solvents are as follows:

[0053]

[0054] serial number

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Abstract

The invention discloses a preparation method and application of a chiral tertiary alcohol or tertiary ether compound. A racemase 4-substituted-4-vinyl-1,3-dioxolan-2-one compound is used as a raw material, and under the catalysis of a palladium coordination compound, which is generated under a palladium source and the coordination action of a chiral ligand, and a boron compound which serve as catalysts, reacts with water or alcohol to prepare the chiral tertiary alcohol or tertiary ether compound. The chiral compound provided by the invention is the multi-functionalized chiral tertiary alcohol or tertiary ether compound, can be used for flexibly and conveniently carrying out functional conversion, is about to be an important chiral molecular building block for preparing a chiral drug and an intermediate. The preparation method provided by the invention comprises asymmetric hydroxylation and etherification reactions co-catalyzed by palladium and boron; the preparation method is high in catalytic activity, high in regioselectivity and enantioselectivity and mild in reaction condition; reactive raw materials are conveniently and easily obtained.

Description

technical field [0001] The invention relates to a preparation method of a compound in the technical field of chemical industry, in particular to a preparation method and application of a chiral tertiary alcohol or tertiary ether compound. Background technique [0002] Chiral tertiary alcohols and tertiary ethers are important structural units of various drugs and natural products with physiological activities. Compared with the preparation of chiral secondary alcohols and secondary ethers, the construction of chiral tertiary alcohols and tertiary ethers has always been a challenging topic in the field of asymmetric synthesis. The asymmetric synthesis of chiral tertiary alcohols mainly relies on the asymmetric addition of carbon nucleophiles to ketones (Shibasaki, M.; Kanai, M. Chem. Rev. 2008, 108, 2853). However, this reaction usually requires the activation of the ketone carbonyl to provide the electrophilic ability of the ketone, and in order to obtain high stereoselecti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B53/00C07C29/12C07C33/30C07C41/16C07C43/178C07C43/23C07C29/132C07C33/46C07C33/48C07D307/28C07D317/54C07D307/42C07D333/16C07C45/64C07C49/255C07C201/12C07C205/34C07C253/30C07C255/13
CPCC07B53/00C07B2200/07C07C29/12C07C29/132C07C41/16C07C41/26C07C45/64C07C201/12C07C253/30C07D301/14C07D303/14C07D307/28C07D307/42C07D317/54C07D333/16C07C33/30C07C43/1787C07C33/46C07C43/23C07C33/48C07C49/255C07C205/34C07C255/13
Inventor 张勇健阿尔玛萨达拉兹伊贾兹赵灿
Owner SHANGHAI JIAO TONG UNIV
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