LU600467B1 - A novel chiral tertiary amine-hydroxyl ligand and preparation method, application - Google Patents

A novel chiral tertiary amine-hydroxyl ligand and preparation method, application

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Publication number
LU600467B1
LU600467B1 LU600467A LU600467A LU600467B1 LU 600467 B1 LU600467 B1 LU 600467B1 LU 600467 A LU600467 A LU 600467A LU 600467 A LU600467 A LU 600467A LU 600467 B1 LU600467 B1 LU 600467B1
Authority
LU
Luxembourg
Prior art keywords
ligand
tertiary amine
chiral
group
mmol
Prior art date
Application number
LU600467A
Other languages
English (en)
Inventor
Yu Zhao
Original Assignee
Univ Yanan
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Univ Yanan filed Critical Univ Yanan
Priority to LU600467A priority Critical patent/LU600467B1/en
Application granted granted Critical
Publication of LU600467B1 publication Critical patent/LU600467B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (5)

Patentanspriiche LU600467
1.Ein neuartiges chirales tertiäres Amin-Hydroxyl-Ligand, wobei es eine chemische Strukturformel aufweist, die wie folgt gezeigt ist: RZ R® 0 ÿ< ; ANR OH {NR wobei R! für Wasserstoff, eine Methylgruppe, eine Benzylgruppe oder eine Boc-Gruppe steht; R° für eine Arylgruppe oder eine Alkylgruppe steht; R* für eine Phenylgruppe oder Wasserstoff steht.
2.Fin Verfahren zur Herstellung des neuartigen chiralen tertiären Amin-Hydroxyl-Liganden gemäB Anspruch 1, umfasst: Ein chirales Amin-Alkohol wird mit einer chiralen N-substituierten Aminosäure kondensiert, um das neuartige chirale tertäre Amin-Hydroxyl-Ligand zu erhalten; die chemische Reaktionsgleichung ist wie folgt: RZ RS N O + & Non Sorts on RY LR x EDCI, DMAP ~~ sh [mt CHL (NR HN OH So ~
3.Das Verfahren zur Herstellung des neuartigen chiralen tertiären Amin-Hydroxyl-Liganden gemäß Anspruch 2, wobei die Kondensation des chiralen Amin-Alkohols mit einer chiralen N- substituierten Aminosäure umfasst:
1.0 Aquivalente N-substituierte Aminosäuren, 1.0 Aquivalente EDCI und 0.1 Aquivalente DMAP werden in CH>Cl> gerührt, um eine Primärlôsung zu erhalten. Diese Primärlôsung wird dann mit
1.0 Aquivalent chiralem Amin-Alkohol versetzt und bei Raumtemperatur für 24-48 Stunden umgesetzt. Nachdem die Reaktion abgeschlossen ist, wird eme Mischungslôsung erhalten, die mittels Petrolether-Fthylacetat-CH:Cl> als Fluens durch Säulenchromatografie gereinigt wird, um das neuartige chirale tertiäre Amin-Hydroxyl-Ligand zu erhalten.
4 Das Verfahren zur Herstellung des neuartigen chiralen tertiären Amin-Hydroxyl-Liganden gemäß Anspruch 3, wobei das Volumenverhältnis von Petrolether zu Ethylacetat zu CH:Cl> des Eluens 1 zu dem Verhältnis von (5-2): 1:1 beträgt.
5. Die Anwendung eines neuen chiralen tertiären Amin-Hydroxy-Liganden als Katalysator für die asymmetrische Addition von Diäthylzink an Aldehyde.
LU600467A 2025-03-05 2025-03-05 A novel chiral tertiary amine-hydroxyl ligand and preparation method, application LU600467B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
LU600467A LU600467B1 (en) 2025-03-05 2025-03-05 A novel chiral tertiary amine-hydroxyl ligand and preparation method, application

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
LU600467A LU600467B1 (en) 2025-03-05 2025-03-05 A novel chiral tertiary amine-hydroxyl ligand and preparation method, application

Publications (1)

Publication Number Publication Date
LU600467B1 true LU600467B1 (en) 2025-09-05

Family

ID=96922238

Family Applications (1)

Application Number Title Priority Date Filing Date
LU600467A LU600467B1 (en) 2025-03-05 2025-03-05 A novel chiral tertiary amine-hydroxyl ligand and preparation method, application

Country Status (1)

Country Link
LU (1) LU600467B1 (de)

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Effective date: 20250905