Tetrahydroquinoline and indoline derivative phosphor nitrogen ligand, synthesis and uses thereof

A technology of tetrahydroquinoline and indoline, which is applied in the field of phosphorus nitrogen compounds, can solve the problems of complex synthesis, difficult recrystallization and purification, and achieve the effects of high regioselectivity, convenient purification and high yield

Active Publication Date: 2009-08-19
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

The ligands of such foamy solids are not only complex to synthesize and difficult to purify by recrystallization, but also have some limitations in metal-catalyzed asymmetric reactions

Method used

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  • Tetrahydroquinoline and indoline derivative phosphor nitrogen ligand, synthesis and uses thereof
  • Tetrahydroquinoline and indoline derivative phosphor nitrogen ligand, synthesis and uses thereof
  • Tetrahydroquinoline and indoline derivative phosphor nitrogen ligand, synthesis and uses thereof

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Embodiment 1

[0020] Embodiment 1: Synthesis based on chiral binaphthyl diphenol phosphorus nitrogen compounds:

[0021]

[0022] Under the protection of argon, in a dry 250 ml three-necked flask, add toluene (50 mL) and triphenylphosphine (0.67 mL, 7.7 mmol), cool to 0 ° C; in another dry 25 ml flask , chiral tetrahydroquinoline and indoline derivatives (7.7mmol), toluene (8mL), and triethylamine (1.8mL, 12.9mmol) were added, and then gradually added dropwise to the above 250ml flask. After the dropwise addition, the temperature was raised to 80°C for 6 hours, and then gradually cooled to -78°C. A solution of R or S binaphthol (bBINOL) (7.0 mmol) and triethylamine (3.5 mL, 25.2 mmol) in toluene (30 mL) and tetrahydrofuran (6 mL) was added slowly to the system. The system was stirred overnight at room temperature (rt), filtered through celite, the solvent was distilled off under reduced pressure, and the crude product was separated by column chromatography (petroleum ether / ethyl acetate...

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Abstract

The invention provides a phosphorus-nitrogen compound based on a binaphthol framework and a synthesis method thereof. The synthesis method is an effective method for synthesizing the optically pure phosphorus-nitrogen compound by taking chiral binaphthol compound, phosphorus trichloride, chiral tetrahydroquinoline and indoline as raw materials under the action of alkali. The method has available raw materials, mild reaction condition and easily separated and purified products. The phosphorus-nitrogen compound which is synthesized by the method based on the binaphthol framework can be effectively applied to an allylic substitution reaction catalyzed by metal iridium, and the product can be obtained at high enantioselectivity and regioselectivity, which greatly expands substrate range of the reaction.

Description

technical field [0001] The present invention relates to a kind of phosphorus nitrogen compound of chiral binaphthyl diol skeleton, synthesis method and application, this method can synthesize this kind of ligand with high yield, and this ligand is successfully applied to 3-indole- Asymmetric synthesis of 1-propene compounds, this type of ligand can be applied in various metal-catalyzed asymmetric reactions. Background technique [0002] Phosphorus-nitrogen compounds based on optically pure binaphthyl diol skeletons are widely used in transition metal-catalyzed reactions to form carbon-carbon bonds and carbon-heterobond bonds, and can synthesize target compounds with high enantioselectivity and regioselectivity. Among them, Ferringa ligands and their derivatives are represented [(a) Feringa, B.L.Acc.Chem.Res.2000, 33, 346. (b) Minnaard, A.J.; Feringa, B.L.Lefort, L.; de Vries, J.G.; Acc.Chem.Res.2007, 40, 1267. (c) Alexakis, A.; Rosset, S.; Allamand, J.; March, S.; Guillen, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6571B01J31/24C07B53/00C07D209/08
CPCB01J2531/827B01J2231/44C07B53/00C07D209/08C07F9/657154B01J31/1845
Inventor 游书力刘文博
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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