Synthetic method for chiral quaternary carbon oxazolidinone compound

A technology of carbooxazolinone and synthesis method, which is applied in the field of catalytic synthesis of chiral quaternary carbooxazolinone compounds, can solve the problems of low stereoselectivity, wide substrate range, complex catalyst, etc. Good selectivity, excellent corresponding selectivity, easy to purify

Inactive Publication Date: 2015-03-25
SUZHOU UNIV
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  • Application Information

AI Technical Summary

Benefits of technology

This patented technology allows for efficient production of various types of chemicals that can be used in industry or research purposes through specific reactions between different starting substances like hydroxylchloroquinalbonyl (HQ) binaphthoxyene-2-carboximide(BZO2) and 2-(methanesulfonylamino)-N'-(2-aminophenylethylenediaminetrimidinedithian-4)) mononucloradium salt complexes). These methods provide improved yields due to simplified operations while maintaining good stereoselective properties.

Problems solved by technology

The technical problem addressed by this patented technology relating to chemical reactions for producing various types of chirality-containing materials with unique properties that could potentially provide useful applications or improve their performance over time without causing negative health consequences. Existing techniques involve expensive starting material sources, complicated processes, difficult reaction conditions, limited choices between different configurations, and lacking flexibility towards changing structures during production process.

Method used

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  • Synthetic method for chiral quaternary carbon oxazolidinone compound
  • Synthetic method for chiral quaternary carbon oxazolidinone compound
  • Synthetic method for chiral quaternary carbon oxazolidinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Add chiral quinine thiourea (2.8 mg, 0.005 mmol), 2a (25.9 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain the target product 5a (5 mg), white solid, 10% yield, >20 / 1 dr, 30% ee.

[0029] Chiral quinine thiourea (5.6 mg, 0.01 mmol), 2a (25.9 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain the target product 5a (27.2 mg), white solid, 55% yield, >20 / 1 dr, 70% ee.

[0030] Chiral quinine thiourea (11.2 mg, 0.02 mmol), 2a (25.9 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethy...

Embodiment 2

[0033]

[0034] Add chiral quinine thiourea (11.2 mg, 0.02 mmol), 2b (27.7 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain the target product 5b (40.0 mg), white solid, 78% yield, >20 / 1 dr, 91% ee.

[0035]Add chiral quinine thiourea (11.2 mg, 0.02 mmol), 2b (27.7 mg, 0.1 mmol), 3a (35.5 mg, 0.15 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain the target product 5b (30.8 mg), white solid, 60% yield, >20 / 1 dr, 91% ee.

[0036] Chiral quinine thiourea (11.2 mg, 0.02 mmol), 2b (27.7 mg, 0.1 mmol), 3a (23.7 mg, 0.1 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (elue...

Embodiment 3

[0039]

[0040] Chiral quinine thiourea (11.2 mg, 0.02 mmol), 2c (33.8 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol), 4? Toluene, reacted at minus 30 degrees Celsius for 12 hours, the reaction system can be obtained by simple column chromatography (eluent: ethyl acetate: petroleum ether = 1:10) to obtain the target product 5c (56.2 mg), white solid, 98% yield, >20 / 1 dr, 94% ee.

[0041] Add chiral quinine thiourea (11.2 mg, 0.02 mmol), and 2c (33.8 mg, 0.1 mmol), 3a (47.4 mg, 0.2 mmol) sequentially into the reaction flask, add 1.5 mL m-xylene, and store at minus 30 degrees Celsius The reaction was carried out for 12 hours, and the reaction system was subjected to simple column chromatography (eluent: ethyl acetate:petroleum ether=1:10) to obtain the target product 5c (40.1 mg), white solid, 70% yield, >20 / 1 dr, 94% ee.

[0042] The product 5c was analyzed and the results are as follows: Determination by HPLC [Daicel Chiralcel AD-H, hexane / i-PrOH(70:30) , flow rate: 1.0 mL·min-1, ...

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Abstract

The invention discloses a synthetic method for a chiral quaternary carbon oxazolidinone compound. The synthetic method comprises the following steps: taking o-hydroxy chalcone and azlactone as reactants and synthesizing in a solvent under the catalysis of chiral multifunctional chiral quinine thiourea to obtain a product. The synthetic method disclosed by the invention has the advantages that raw materials are easy to obtain, the reaction conditions are mild, the post-treatment is simple and convenient, the applicable substrate scope is wide, the yield is high, and the enantioselectivity is high; the product obtained by the synthesis method can be used for synthesizing an intermediate of a drug and a pesticide.

Description

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Claims

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Application Information

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Owner SUZHOU UNIV
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