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Method of asymmetrically compounding chirality diaryl methyl alcohol

A technology of diaryl carbinol and synthesis method, which is applied in the field of asymmetric synthesis of chiral diaryl carbinol to achieve high-efficiency stereoselective effect

Active Publication Date: 2015-07-29
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There is no bibliographical report for the method of synthesizing chiral diaryl carbinols by rhodium-catalyzed nucleophilic addition of boronic acid to aromatic aldehydes with nitrogen heterocyclic carbene salts

Method used

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  • Method of asymmetrically compounding chirality diaryl methyl alcohol
  • Method of asymmetrically compounding chirality diaryl methyl alcohol
  • Method of asymmetrically compounding chirality diaryl methyl alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The synthesis of embodiment 1 (S)-2-chlorophenyl benzyl alcohol

[0021] The reaction formula is:

[0022]

[0023] Under nitrogen protection, 5mmol benzaldehyde and 5.5mmol 2-chlorophenylboronic acid, 0.1mmol Cs 2 CO 3 , 0.05mmol chiral azacyclic ferrocene salt and 0.025mmol rhodium compound were added to a strictly dry reaction flask, then 5mL of absolutely anhydrous dichloromethane was injected into the reaction flask, the stopper was sealed, and stirred at 50°C After reacting for 6h, stop stirring, add 5mL of water, and then stir for 1h. Filter, separate the organic layer, wash the aqueous layer twice with dichloromethane, combine the organic layers, dry over anhydrous sodium sulfate, and evaporate the solvent under reduced pressure to obtain a crude product, which is separated and purified by a silica gel column to obtain the product. The yield : 90%.

[0024] A small amount of the compound prepared above was dissolved in isopropanol-hexane (3:7) solvent, an...

Embodiment 2

[0025] The synthesis of embodiment 2 (S)-2-bromophenyl-4-methylbenzyl alcohol

[0026] The reaction formula is:

[0027]

[0028] Under nitrogen protection, add 5mmol 4-methylbenzaldehyde and 5.5mmol 2-bromophenylboronic acid, 0.15mmol KOAc, 0.06mmol chiral azacyclic ferrocene salt and 0.025mmol rhodium compound into a strictly dry reaction flask , then inject 5 mL of absolutely anhydrous toluene into the reaction bottle, seal the stopper, stir and react at 45°C for 7 h, stop stirring, add 5 mL of water, and then stir for 1 h. Filter, separate the organic layer, wash the aqueous layer twice with toluene, combine the organic layers, dry over anhydrous sodium sulfate, and evaporate the solvent under reduced pressure to obtain a crude product, which is separated and purified by a silica gel column to obtain the product, yield: 87 %.

[0029] A small amount of the compound prepared above was dissolved in isopropanol-hexane (3:7) solvent, and chiral liquid chromatography was u...

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Abstract

The invention discloses a method of asymmetrically compounding diaryl methyl alcohol. The equation of the compounding method refers to the Specification. In the equation, R1 and R2 are groups in an aromatic ring; a catalyzer is chirality nitrogen heterocycle ferrocene carbene salt; alkali is acetate, carbonate, bicarbonate, organic amine of alkali metal and the like. The method provides a novel and efficient method high in stereoselectivity for asymmetrical compound of chirality diaryl methyl alcohol.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for asymmetrically synthesizing chiral diaryl carbinol. Background technique [0002] Chiral diaryl carbinol is an important class of intermediates and molecular fragments, which widely exist in natural and unnatural molecules with physiological and pharmacological activities, and can also be used to synthesize biologically active compounds or drugs such as diuretics, Antidepressants, local anesthetics, antihistamines, etc.; due to the wide range of uses of chiral diaryl carbinols, research on methods for preparing diaryl carbinols with high stereoselectivity has attracted great attention from chemical workers. [0003] The common asymmetric catalytic synthesis of diarylmethanols can be summarized into two main methods: one is through the arylation reaction of aromatic aldehydes and aryl transfer reagents; the other is through the asymmetric reducti...

Claims

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Application Information

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IPC IPC(8): C07C33/46C07C29/14
CPCC07B53/00C07B2200/07C07C29/14C07C33/46
Inventor 程青芳王启发王静文
Owner HUAIHAI INST OF TECH