Diphenylamine-linked chiral bis(oxazoline) ligand without C2-symmetry, synthesis method and application thereof

US12545651B2 · US · B2

Patent metadata
FieldValue
Publication numberUS-12545651-B2
Application numberUS-202017614752-A
CountryUS
Kind codeB2
Filing dateApr 30, 2020
Priority dateMay 31, 2019
Publication dateFeb 10, 2026
Grant dateFeb 10, 2026

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  1. Title

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  2. Abstract

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  5. First independent claim

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Abstract

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The present invention discloses a diphenylamine-linked chiral bis(oxazoline) ligand without C 2 -symmetry of formula 3 and its synthesis method and application in an asymmetric catalytic reaction, wherein C 2 -symmetry is lost by introducing different groups into the diphenylamine backbone to realize precise control of “electronic effect” of the ligand backbone. An anthranilic acid derivative and an orthochlorobenzoic acid derivative are used as starting materials to prepare a compound of formula 1, and then the compound of formula 1 is reacted with a chiral amino alcohol compound to prepare a β-bishydroxy amide compound of formula 2, and the compound of formula 2 is further subjected to condensation to obtain the diphenylamine-linked chiral bis(oxazoline) ligand without C 2 -symmetry of formula 3. The present invention also provides an application of a catalyst formed by coordination of the diphenylamine-linked chiral bis(oxazoline) ligand without C 2 -symmetry with copper salt, zinc salt, nickel salt, iron salt or rhodium salt, in an asymmetric catalytic reaction.

First claim

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The invention claimed is: 1 . A diphenylamine-linked chiral bis(oxazoline) ligand without C 2 -symmetry selected from one of the following:

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Classifications

  • with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

  • Zinc · CPC title

  • Copper · CPC title

  • Allylic alkylation, amination, alkoxylation or analogues · CPC title

  • Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions · CPC title

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What does patent US12545651B2 cover?
The present invention discloses a diphenylamine-linked chiral bis(oxazoline) ligand without C 2 -symmetry of formula 3 and its synthesis method and application in an asymmetric catalytic reaction, wherein C 2 -symmetry is lost by introducing different groups into the diphenylamine backbone to realize precise control of “electronic effect” of the ligand backbone. An anthranilic acid derivative a…
Who is the assignee on this patent?
Univ Zhejiang Technology
What technology area does this patent fall under?
Primary CPC classification C07D263/14. Mapped technology areas include Chemistry & Metallurgy.
When was this patent published?
Publication date Tue Feb 10 2026 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
What related patents are in patentsdb?
We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).