Chiral diamine diphosphine metal compound catalysts as well as preparation method and application thereof

Abstract

The invention discloses chiral diamine diphosphine metal compound catalysts as well as a preparation method and an application thereof and relates to heteroatomic ring phosphine group-containing chiral diamine diphosphine late transition metal compound catalysts and a preparation method thereof. PCl2(NEt2) is selectively synthesized from low-price PCl3 beginner by reaction with NEt2H, then PR2Cl containing two heteroatomic ring groups (R represents different heteroatomic ring groups shown in the patent) is synthesized by twice group exchange reactions, and finally a series of diamine diphosphine chiral ligands containing different heteroatom-substituted cyclic aryl phosphine groups and late transition metal compound catalysts thereof can be synthesized from PR2Cl as precursor. The catalysts can be used for asymmetric transfer hydrogenation of aromatic ketone. The transformation rate and the enantioselectivity of the catalysts in catalytic transformation of chiral aromatic alcohols from aromatic ketone are up to 97.1% and 99.5% respectively.

Description

technical field [0001] The invention relates to a chiral diamine bisphosphine post-transition metal compound catalyst containing a heteroatom ring phosphine group and a preparation method thereof, and a method for catalyzing the asymmetric transfer hydrogenation of aromatic ketones by the metal compound catalyst. Background technique [0002] At present, most chiral molecules can be synthesized by asymmetric catalysis. In asymmetric catalysis, chiral ligand-bound metals or chiral ligand-metal compounds play a role in the stereoregulation of the synthesis of these molecules. The chiral ligands of PNNP structure are a very important class of ligands, which can be effectively used in the preparation of optically active alcohols, and optically active alcohols are the main intermediates for the preparation of α-aromatic amine alcohol chiral drugs, such as bronchial dilator salbutamol (Salbutamo), antidepressant fluoxetine (Fluaxetine), etc. In 1996, Widhalm (J.Organomet.Chem., ...

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Problems solved by technology

In 1996, Widhalm (J.Organomet.Chem., 1996,523:167) reported the PNNP chiral ligand as structural formula I-A, the ruthenium compound of this ligand can be used for carbon-carbon asymmetric coupling catalytic reaction, but the product The ee value is not very good; in the same year, Trost et al. (J.Am.Chem.Soc., 1996, 118:6520) reported that the PNNP chiral ligand as shown in Figure I-C, combined with metal palladium compound can asymmetrically catalyze the containing Deesterification carbon-carbon coupling reaction of alkenyl group, the ee selectivity of the product varies from 29% to 92%

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