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Phenol derivatives containing (Sp)-2-chiral phosphinate substituent groups and preparation method thereof

A technology of phosphinate and substituents, which is applied in the field of phenolic derivatives containing 2-chiral phosphinate substituents and the preparation thereof, can solve the problem of difficult recycling of chiral resolution reagents, resolution reagents Low activity and selectivity, harsh reaction conditions, etc., to achieve good industrial application prospects, cheap catalysts, and simple preparation

Active Publication Date: 2013-09-18
HUNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods generally use relatively expensive chiral catalysts, and the experimental steps are cumbersome, the reaction conditions are harsh, and the yield is low; even if some chiral resolution methods are used, the activity and selectivity of the resolving agent are generally low. Moreover, chiral resolution reagents are difficult to recycle

Method used

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  • Phenol derivatives containing (Sp)-2-chiral phosphinate substituent groups and preparation method thereof
  • Phenol derivatives containing (Sp)-2-chiral phosphinate substituent groups and preparation method thereof
  • Phenol derivatives containing (Sp)-2-chiral phosphinate substituent groups and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Take 0.280 g (1.0 mmol) Rp-phenylphosphinic acid-(-)-menthol ester, 220 mg (1.0 mmol) 2-iodo-phenol, 489 mg (1.5 mmol) cesium carbonate, 2.0 mL N,N- Add dimethylformamide and 3.0 mL toluene to the Schlenk tube under nitrogen atmosphere, add 115.6 mg (0.1 mmol) palladium tetrakistriphenylphosphine, o The reaction was stirred at C for 12 h to obtain the target product Sp-(-)-menthol-2-hydroxyphenyl-phenylphosphinate with a yield of 73%.

Embodiment 2

[0030] Take 0.280 g (1.0 mmol) Rp-phenylphosphinic acid-(-)-menthol ester, 226.6 mg (1.03 mmol) 2-iodo-phenol, 212 mg (1.0 mmol) potassium phosphate and 5.0 mL toluene in a nitrogen atmosphere Add 5.94 mg (0.06 mmol) cuprous chloride to the Schlenk tube at 100 o The reaction was stirred at C for 13 h to obtain the target product Sp-(-)-menthol-2-hydroxyphenyl-phenylphosphinate with a yield of 76%.

Embodiment 3

[0032] Take 0.280 g (1.0 mmol) Rp-phenylphosphinic acid-(-)-menthol ester, 231 mg (1.05 mmol) 2-iodo-phenol, 179.4 mg (1.3 mmol) potassium carbonate and 3.0 mL 1,4- Dioxane was added to the Schlenk tube under nitrogen atmosphere, and 11.4 mg (0.08 mmol) of cuprous bromide was added, at 80 o The reaction was stirred at C for 16 h to obtain the target product Sp-(-)-menthol-2-hydroxyphenyl-phenylphosphinate with a yield of 82%.

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Abstract

The invention provides a method for synthesizing phenol derivatives containing (Sp)-2-chiral phosphinate substituent groups with a phosphorus chiral center at high stereoselectivity. The method is characterized in that an organic small molecule material is taken as a catalyst, (Rp)-chiral phosphinate compounds containing a P-H bond and 2-halogenated phenol (-I, -Br) are taken as reaction substrates, and a base and an organic solvent are added to a reaction system. The method provided by the invention has the following advantages that the catalyst is cheap and easy to obtain, the reaction conditions are mild, and safe and reliable, the stereoselectivity of the obtained target product is close to 100% and the yield of the product is high; and the method overcomes the shortcomings of poor stereo enantioselectivity, complex reaction steps, low yield and the like of the traditional method for synthesizing a chiral phosphine compound with the phosphorus chiral center, and has an excellent industrial application prospect. The invention also provides phenol derivatives containing the (Sp)-2-chiral phosphinate substituent groups with the phosphorus chiral center.

Description

【Technical field】 [0001] The invention relates to the field of asymmetric catalytic synthesis of organic phosphine compounds with a phosphorus chiral center, in particular to a phenol derivative containing (Sp)-2-chiral phosphinate substituents with a phosphorus chiral center substances and their preparation methods. 【Background technique】 [0002] Organic (phosphino)phosphonate compounds with phosphorus chiral centers are an important class of organic compounds, which have good optical activity and biological activity, making them useful in biology, medicine, optically active materials and asymmetric catalytic synthesis. and so on have a wide range of applications. However, it is difficult to find natural optically active chiral organophosphorus compounds in nature, and most of the known organophosphorus compounds with phosphorus chiral centers are synthesized by chemical methods. [0003] In recent years, with the continuous expansion of the application field of chiral o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/32
Inventor 尹双凤熊碧权周永波韩立彪
Owner HUNAN UNIV
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