Preparation methods and applications of chiral spirophosphine-nitrogen-phosphine tridentate ligand and iridium catalyst thereof

A catalyst and spiro ring technology, which is applied in the field of organic synthesis, can solve the problems such as the difficulty in recognizing the chirality of the carbonyl plane of the substrate by the catalyst, and achieve the effects of excellent enantioselectivity, mild reaction conditions and great practical value.
CN111484533AActive Publication Date: 2020-08-04ZHEJIANG JIUZHOU PHARM CO LTD
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
ZHEJIANG JIUZHOU PHARM CO LTD
Publication Date
2020-08-04

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Abstract

The invention relates to preparation methods and applications of a chiral spirophosphine-nitrogen-phosphine tridentate ligand SpiroPNP and an iridium catalyst Ir-SpiroPNP thereof. The chiral spirophosphine-nitrogen-phosphine tridentate ligand is a compound represented by a formula I, or a racemate or an optical isomer thereof, or a catalytically acceptable salt thereof, and is mainly structurallycharacterized by having a chiral spiro indane skeleton and a phosphine ligand with a large steric hindrance substituent. The chiral spirophosphine-nitrogen-phosphine tridentate ligand can be synthesized by taking a 7-diaryl / alkylphosphino-7'-amino-1,1'-spiro indane compound with a spiro skeleton as a chiral starting raw material. The iridium catalyst of the chiral spirophosphine-nitrogen-phosphinetridentate ligand is a compound represented by a formula II which is described in the specification, or a raceme or an optical isomer, or a catalytically acceptable salt thereof, can be used for catalyzing asymmetric catalytic hydrogenation reaction of carbonyl compounds, particularly shows high yield (greater than 99%) and enantioselectivity (as high as 99.8% ee) in asymmetric hydrogenation reaction of simple dialkyl ketone, and has practical value.
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Description

technical field

[0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method and application of a class of chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligands and iridium catalysts thereof, in particular to a class of chiral phosphine-nitrogen-phosphine with a spiro ring skeleton Preparation method of tridentate ligand and its iridium catalyst and application in asymmetric catalytic hydrogenation of simple dialkyl ketones. Background technique

[0002] Transition metal asymmetric catalytic hydrogenation has the advantages of high atom economy, mild reaction conditions, high catalytic activity, and good enantioselectivity. It has become one of the most simple, convenient and efficient methods to obtain chiral molecules, and has It has been widely used in the industrial production of drug molecules and chiral pesticides, such as L-dopa, carbapenicillin, Jin Duoer, etc. It is precisely because of their outstanding...

Claims

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