Chiral annular nitrone and preparation method thereof

The intermolecular cyclization reaction of alkenyl oxime and aryl halides catalyzed by palladium catalyst and chiral tert-butylsulfonamide ligand was solved, and the chiral cyclic nitrogen synthesis method was achieved, and the chiral cyclic nitrogen preparation with good enantioselectivity was achieved. The product has a wide application prospect.

CN120441469APending Publication Date: 2025-08-08CHANGCHUN UNIV OF TECH
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Patent Information

Application Number
CN202510452463.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-04-11
Publication Date
2025-08-08

AI Technical Summary

Technical Problem

In the prior art, there are fewer methods for synthesizing chiral cyclic nitrosterone, especially lack of methods for catalyzing chiral nitrosterone, and the existing methods have poor enantioselectivity control and low synthesis efficiency.

Method used

Alkenyl oxime and aryl halide are used as raw materials, and chiral ligand reacted in an inert atmosphere by reacting palladium catalyst and chiral ligand in an inert atmosphere to prepare chiral cyclic nitrosterone, chiral tert-butylsulfinamide ligand and base are used as catalysts to control enantioselectivity and avoid the formation of competitive reaction products.

Benefits of technology

High yield and excellent enantioselectivity are achieved, with a yield of up to 90%, an ee value of up to 98%, mild reaction conditions and a wide range of application. The products can be used for the synthesis of drug-active azocyclic intermediates.

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Abstract

The invention provides chiral annular nitrone and a preparation method thereof, and belongs to the technical field of organic synthetic chemistry. The method comprises the following steps: by taking alkenyl oxime and aryl halide as raw materials, adding a palladium catalyst, a chiral ligand and alkali, then adding an organic solvent under the protection of inert gas, and reacting at 50-100 DEG C for 12-24 hours. And after the reaction is finished, carrying out silica gel column chromatography separation to obtain the chiral annular nitrone. According to the invention, the palladium catalyst is combined with the chiral ligand to realize intermolecular cyclization of alkenyl oxime and aryl halide to generate chiral annular nitrone. The reaction enantioselectivity is good, generation of a Heck product and an oxygen heterocyclic ring product oxime ether is avoided, the highest yield can reach 90%, the highest ee value can reach 98%, the conditions are mild, the yield is high, and the method has a very good application prospect.
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