Novel use of chiral diphosphonic diamide oxazoline

A bisphosphonamide oxazoline, a new application technology, applied in the field of known compounds, can solve the problems of complicated operation and low efficiency

Inactive Publication Date: 2011-02-16
罗梅
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Chiral cyanohydrin can be separated from the racemate, but the operation is complicated and the efficiency is low

Method used

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  • Novel use of chiral diphosphonic diamide oxazoline
  • Novel use of chiral diphosphonic diamide oxazoline
  • Novel use of chiral diphosphonic diamide oxazoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0023] R / S-a-Phenylethylamine: Changzhou Kerunda Technology Co., Ltd.

[0024] (1) Preparation of chiral catalyst

[0025] 1. Preparation of intermediate 2-[(4S)-4,5-dihydro-4-(1',1'-dimethylethyl)-2-oxazolinyl]aniline

[0026] In a 100mL two-necked bottle, under anhydrous and anaerobic conditions, add anhydrous ZnCl 2 60mg (0.37mmol), 40mL chlorobenzene, 1.0g (8.47mmol) of 2-cyanoaniline, L-phenylglycinol 3g, the mixture was refluxed at high temperature for 24h, the reaction was stopped, and the solvent was removed under reduced pressure, and the remaining The substance was dissolved in water and washed with CHCl 3 (20mLx2) extraction, the organic phase was dried with anhydrous sodium sulfate, and the solvent was removed by rotation, and the crude product was subjected to column chromatography with petroleum ether / dichloromethane (4:1) to obtain a colorless oily liquid with a yield of 58%; [a ] 5 D =195.8° (c=0.25, CHCl 3 ): 1 HNMR (500MHz, CDCl 3 , 27℃), δ(ppm)=7.74(...

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Abstract

A chiral phosphonic diamide compound is N,N-2-[(4S)-4,5-dihydro-4-R-2-oxazoline]diphenyl-phenyl phosphonic diamide, and has a chemical formula. A synthesis method for the compound comprises the following steps of: refluxing and reacting 2-cyanoaniline and L-phenylglycinol for 24 hours in a chlorobenzene solvent under the conditions of no water and no oxygen and in the presence of a catalyst ZnCl2 to prepare an intermediate, and refluxing and reacting the intermediate and diphenyl phosphonic chloride for 24 hours in a methylbenzene-triethylamine mixed solvent under the conditions of no water and no oxygen to synthesize the target product. When the chiral target product is prepared by the cyanation-silication reaction of 4-methylbenzaldehyde, 4-methoxybenzaldehyde and 4-bromobenzaldehyde, the compound serves as a chiral catalyst.

Description

1. Technical field [0001] The present invention relates to a new application of a known compound, in particular to a new application of oxazoline, to be precise a new application of chiral chiral bisphosphonamide oxazoline in asymmetric catalytic reaction. 2. Background technology [0002] Cyanohydrin compounds are important intermediates in organic synthesis, especially chiral aryl cyanohydrin is an important pharmaceutical intermediate. Therefore, the addition reaction of carbonyl, especially aromatic aldehyde, with cyanide or nitrile has been extensively studied. [0003] Chiral cyanohydrins can be separated from racemates, but the operation is complicated and the efficiency is low. If a chiral catalyst is used, it can be obtained directly by synthesis. 3. Contents of the invention [0004] The invention aims at preparing chiral target products for the addition reaction of aromatic aldehydes and cyanides or nitriles, and the technical problem to be solved is to provid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02C07F7/18C07B53/00
Inventor 罗梅
Owner 罗梅
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