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

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, ...

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