Chiral 1-phospha norborneol diene derivative and synthesis method thereof

A technology of norbornanyl and phosphata, which is applied in the field of 1-phosphanorbornadiene compounds and their synthesis, achieving the effects of high yield, broad commercial application prospects, and simple synthesis methods

Inactive Publication Date: 2019-01-18
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] So far, the design of chiral phosphorus-oxygen ligands with phosphorus chir

Method used

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  • Chiral 1-phospha norborneol diene derivative and synthesis method thereof
  • Chiral 1-phospha norborneol diene derivative and synthesis method thereof
  • Chiral 1-phospha norborneol diene derivative and synthesis method thereof

Examples

Experimental program
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Embodiment 1

[0021]

[0022] (1) in N 2 Under ambient conditions, add 40mL of methanol, phenylpropynaldehyde (20mmol), and trimethyl orthoformate (40mmol) into a 100mL Schlenk bottle, then add the catalyst p-toluenesulfonic acid (10mol%), and transfer to a 65°C oil bath to reflux for 10h. After the reaction was complete, a small amount of solid NaOH was added, and stirring was continued for 20 min. After rotary evaporation under reduced pressure, the compound A2 was obtained after passing through a neutral alumina drying column with a yield of 93%.

[0023]

[0024] (2) in N 2 At ambient, 5 mL of toluene, compound A2 (5.6 mmol), phosphole (5.3 mmol) were added to a 75 mL Schlenk bottle. React in an oil bath at 140°C for 2h. After passing through a neutral alumina column (PE:DCM=10:1), compound A3 was obtained. Yield 80%.

[0025] (3) in N 2 Under ambient conditions, add 20 mL of dichloromethane, compound A3, hydrochloric acid, and silicon dioxide into a 100 mL Schlenk bottle, a...

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Abstract

The invention belongs to the field of organic chemical synthesis, and particularly relates to a 1-phospha norborneol diene derivative with application values in the asymmetric catalysis field and a synthesis method thereof. A series of phosphorus chiral center chiral phosphorous ligands are synthesized; a 1-phospha norborneol diene framework and a chiral sulphoxide type compound are combined; wideapplication prospects are realized in the asymmetrical synthesis field. The derivative has the following structure general formula shown in description.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to 1-phosphanorbornadiene compounds used in the field of asymmetric catalysis and a synthesis method thereof. Background technique [0002] In the field of asymmetric catalysis, chiral organophosphides are important ligands or catalysts. Due to the lone pair of electrons, trivalent organophosphides can be used as ligands to complex with metals to form metal complexes, participate in asymmetric reactions catalyzed by metals, and act as catalysts to attack electron-deficient alkenes to generate carbanions. , and catalyze chemical reactions. In previous studies, chemists focused on the selection of the chiral backbone linked to phosphorus, that is, the chirality of the target product is generated through the induction of the chiral backbone. Because of the nature of phosphorus itself, the phosphorus chiral center is difficult to synthesize and easy to racemize at high temper...

Claims

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Application Information

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IPC IPC(8): C07F9/6568
CPCC07F9/65683
Inventor 段征李二庆支梦娜甘贞洁
Owner ZHENGZHOU UNIV
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