A method for synthesizing chiral dihydrocoumarins by palladium-catalyzed asymmetric hydrogenation of tetrasubstituted olefins

By using palladium-catalyzed complex catalysts of tetrasubstituted olefins and chiral bisphosphine ligands, the problems of high efficiency, simplicity, and environmental friendliness in the synthesis of chiral dihydrocoumarins in existing technologies have been solved, achieving highly selective and high-yield asymmetric hydrogenation synthesis of chiral dihydrocoumarins.

CN118084843BActive Publication Date: 2026-01-30DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES
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Patent Information

Application Number
CN202211449257.6
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2022-11-18
Publication Date
2026-01-30
Estimated Expiration
2042-11-18

AI Technical Summary

Technical Problem

Existing technologies are difficult to synthesize chiral dihydrocoumarins efficiently and easily, especially in terms of high enantioselectivity and diastereoselectivity, and the reaction is not green and environmentally friendly enough.

Method used

Chiral dihydrocoumarin was synthesized via asymmetric hydrogenation using a palladium-catalyzed complex of a tetrasubstituted olefin and a chiral bisphosphine ligand as a catalyst. Trifluoroethanol or hexafluoroisopropanol was used as the solvent, the reaction temperature was 20-40℃, and the hydrogen pressure was 300-500psi. The reaction conditions were optimized to improve selectivity and yield.

Benefits of technology

A high-yield, high-enantioselectivity and diastereoselectivity synthesis of chiral dihydrocoumarins was achieved, with simple operation, readily available raw materials, environmental friendliness and low energy consumption.

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Abstract

This invention discloses a palladium-catalyzed asymmetric hydrogenation method for synthesizing chiral dihydrocoumarin from tetrasubstituted olefins. The method uses a chiral bisphosphine complex of palladium as a catalyst and a tetrasubstituted olefin as a substrate to synthesize chiral dihydrocoumarin via asymmetric hydrogenation. This invention employs a homogeneous palladium catalytic system to achieve asymmetric hydrogenation of tetrasubstituted olefins with high yield, high enantioselectivity (up to 99% enantiomeric excess), and high diastereoselectivity (diastereomer ratio >20:1), producing chiral dihydrocoumarin. The method is simple and practical, the catalyst is commercially available, the reaction conditions are mild, energy consumption is low, and it is environmentally friendly.
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