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Chiral organic selenium sulfur catalyst and its preparation method and application in asymmetric reaction

A technology of organic selenium and catalyst, which is applied in the field of chiral organic selenium sulfur catalysis, can solve the problems of inability to complete the asymmetric trifluoromethylthio esterification reaction of alkenes, and achieve excellent optical selectivity, convenient operation, and enantioselectivity Good results

Inactive Publication Date: 2018-03-16
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a novel chiral organic selenium sulfur catalyst and its preparation method to solve the problem of asymmetric trifluoromethylthio esterification of olefins that cannot be completed in the prior art

Method used

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  • Chiral organic selenium sulfur catalyst and its preparation method and application in asymmetric reaction
  • Chiral organic selenium sulfur catalyst and its preparation method and application in asymmetric reaction
  • Chiral organic selenium sulfur catalyst and its preparation method and application in asymmetric reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0019] (1) Put 1.34g of (1S,2R)-(+)-1-amino-2-indanol in a 100mL reaction flask, vacuumize and fill with nitrogen, and repeat this process three times. Then place the reaction bottle in an ice bath and cool it down to 0°C, then add 2.55g Boc 2 0 and 36 mL of redistilled acetonitrile were added to the reactor, and the ice bath was removed and stirred for 5 hours until the solution was clear and transparent, indicating that the reaction had been completed. Spin-dry directly to obtain a viscous liquid, and proceed directly to the next step. The synthetic formula of this step is:

[0020]

[0021] (2) Place the Boc-protected indenaminol prepared above in a 100 mL reaction flask, first vacuumize and fill with nitrogen, and repeat this three times. After adding 30 mL of redistilled dichloromethane, the reaction bottle was cooled to 0°C in an ice bath, and then 2 mL of triethylamine and 1 mL of ethylsulfonyl chloride were added thereto. Allow the ice bath to slowly return to ro...

Embodiment 2

[0029] (1) Put 1.34g of (1S,2R)-(+)-1-amino-2-indanol in a 100mL reaction flask, vacuumize and fill with nitrogen, and repeat this process three times. Then place the reaction bottle in an ice bath and cool it down to 0°C, then add 2.55g Boc 2 0 and 36 mL of redistilled acetonitrile were added to the reactor, and the ice bath was removed and stirred for 5 hours until the solution was clear and transparent, indicating that the reaction had been completed. Spin-dry directly to obtain a viscous liquid, and proceed directly to the next step. The synthetic formula of this step is:

[0030]

[0031] (2) Place the Boc-protected indenaminol prepared above in a 100 mL reaction flask, first vacuumize and fill with nitrogen, and repeat this three times. After adding 30 mL of redistilled dichloromethane, the reaction bottle was cooled to 0°C in an ice bath, and then 2 mL of triethylamine and 1 mL of ethylsulfonyl chloride were added thereto. Allow the ice bath to slowly return to ro...

Embodiment 3

[0038] (1) Put 1.34g of (1R,2S)-(+)-1-amino-2-indanol in a 100mL reaction flask, vacuumize and fill with nitrogen, and repeat this process three times. Then place the reaction bottle in an ice bath and cool it down to 0°C, then add 2.55g Boc 2 0 and 36 mL of redistilled acetonitrile were added to the reactor, and the ice bath was removed and stirred for 5 hours until the solution was clear and transparent, indicating that the reaction had been completed. Spin-dry directly to obtain a viscous liquid, and proceed directly to the next step. The synthetic formula of this step is:

[0039]

[0040] (2) Place the Boc-protected indenaminol prepared above in a 100 mL reaction flask, first vacuumize and fill with nitrogen, and repeat this three times. After adding 30 mL of redistilled dichloromethane, the reaction bottle was cooled to 0°C in an ice bath, and then 2 mL of triethylamine and 1 mL of ethylsulfonyl chloride were added thereto. Allow the ice bath to slowly return to ro...

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Abstract

The invention discloses a chiral organic selenium-sulfur catalyst and its preparation method and use in an asymmetric reaction. The chiral organic selenium-sulfur catalyst is prepared from commercial and low price chiral amino-indanol through high efficiency multi-step synthesis. The preparation method has simple processes and is convenient for operation. The chiral organic selenium-sulfur catalyst based on an organic indene skeleton has a wide application range, good catalysis effects in many organic reactions and excellent enantiomer selectivity. The chiral organic selenium-sulfur catalyst has excellent optical selectivity in an asymmetric trifluoromethylthioesterification reaction, opens the ancient river of an alkene asymmetric trifluoromethylthioesterification reaction and has high catalysis efficiency and good enantioselectivity.

Description

Technical field: [0001] The invention relates to the field of chiral organic selenium-sulfur catalysis, in particular to a chiral organic selenium-sulfur catalyst and its preparation method and application in asymmetric trifluoromethylthio esterification reaction. Background technique: [0002] Organoselenium-sulfur is an important element in the chemical family. In the past 20 years, organoselenium-sulfur chemistry has developed rapidly. New organoselenium-sulfur reagents play an important role in organic synthetic chemistry and are widely used in the synthesis of natural products and medical drugs. . Organoselenosulfur reagents have a variety of chemical properties and can be used as oxidizing agents, reducing agents, nucleophiles and electrophiles, etc. It is worth noting that the selenium-sulfur atoms in organic selenide-sulfur compounds have lone pairs of electrons, which can act as Lewis bases to catalyze certain reactions. Compared with traditional organometallic co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02C07C323/43C07C391/02C07D307/64
CPCB01J31/0245B01J31/0275B01J2231/00C07C323/43C07C391/02C07D307/64
Inventor 赵晓丹刘想
Owner SUN YAT SEN UNIV
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